922:
531:
651:
983:
937:
602:
1007:
968:
953:
481:
393:
745:
614:
20:
631:
react with base to give epoxides. The reaction is spontaneous because the energetic cost of introducing the ring strain (13 kcal/mol) is offset by the larger bond enthalpy of the newly introduced C-O bond (when compared to that of the cleaved C-halogen bond).
635:
Formation of epoxides from secondary halohydrins is predicted to occur faster than from primary halohydrins due to increased entropic effects in the secondary halohydrin, and tertiary halohydrins react (if at all) extremely slowly due to steric crowding.
754:
Epoxides react with a broad range of nucleophiles, for example, alcohols, water, amines, thiols, and even halides. With two often-nearly-equivalent sites of attack, epoxides exemplify "ambident substrates". Ring-opening
355:
2126:
Niederer, Christian; Behra, Renata; Harder, Angela; Schwarzenbach, René P.; Escher, Beate I. (2004). "Mechanistic approaches for evaluating the toxicity of reactive organochlorines and epoxides in green algae".
982:
201:
catalysts are typically employed. According to a reaction mechanism suggested in 1974 at least one ethylene molecule is totally oxidized for every six that are converted to ethylene oxide:
973:
433:
Peroxycarboxylic acids, which are more electrophilic than other peroxides, convert alkenes to epoxides without the intervention of metal catalysts. In specialized applications,
174:
hydroperoxide can be used as oxygen sources during propylene oxidation (although a catalyst is required as well, and most industrial producers use dehydrochlorination instead).
921:
1285:
Nijhuis, T. Alexander; Makkee, Michiel; Moulijn, Jacob A.; Weckhuysen, Bert M. (1 May 2006). "The
Production of Propene Oxide: Catalytic Processes and Recent Developments".
1357:
Thiel W. R. (1997). "Metal catalyzed oxidations. Part 5. Catalytic olefin epoxidation with seven-coordinate oxobisperoxo molybdenum complexes: a mechanistic study".
387:(TBHP). Association of TBHP with the metal (M) generates the active metal peroxy complex containing the MOOR group, which then transfers an O center to the alkene.
967:
763:
2 pattern of attack at the least-substituted carbon, but can be affected by carbocation stability under acidic conditions. This class of reactions is the basis of
1871:
Bruce
Rickborn and Wallace E. Lamke (1967). "Reduction of epoxides. II. The lithium aluminum hydride and mixed hydride reduction of 3-methylcyclohexene oxide".
2071:; Martha A. Umbreit; Marjorie T. Nieh; Thomas C. Flood (1972). "Lower valent tungsten halides. New class of reagents for deoxygenation of organic molecules".
936:
545:
Chiral epoxides can often be derived enantioselectively from prochiral alkenes. Many metal complexes give active catalysts, but the most important involve
530:
499:
may be formed. In addition, if there are other stereocenters present in the starting material, they can influence the stereochemistry of the epoxidation.
204:
1971:
B. Mudryk; T. Cohen (1995). "1,3-Diols From
Lithium Β-lithioalkoxides Generated By The Reductive Lithiation Of Epoxides: 2,5-dimethyl-2,4-hexanediol".
487:
The stereochemistry of the reaction is quite sensitive. Depending on the mechanism of the reaction and the geometry of the alkene starting material,
59:, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and
1179:
1144:
1998:
Takuya
Nakagiri; Masahito Murai; Kazuhiko Takai (2015). "Stereospecific Deoxygenation of Aliphatic Epoxides to Alkenes under Rhenium Catalysis".
1699:"Computational insights into the spontaneity of epoxide formation from halohydrins and other mechanistic details of Williamson's ether synthesis"
425:
to give a stabilized carbanion. This carbanion then attacks the same oxygen atom, displacing a leaving group from it, to close the epoxide ring.
1214:
Dietmar
Kahlich, Uwe Wiechern, Jörg Lindner "Propylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry, 2002 by Wiley-VCH, Weinheim.
1936:(2016). "Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships".
1006:
421:
can be epoxidized using nucleophilic oxygen compounds such as peroxides. The reaction is a two-step mechanism. First the oxygen performs a
103:
O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide
2188:
163:. Safety considerations weigh on these reactions because organic peroxides are prone to spontaneous decomposition or even combustion.
3107:
665:
79:
can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of
3112:
1616:
1671:"(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane"
1819:
1788:
1112:
1916:
1653:
1196:
1161:
952:
521:π electrons to attack. Because two bonds are broken and formed to the epoxide oxygen, this is formally an example of a
1330:
Indictor N., Brill W. F. (1965). "Metal
Acetylacetonate Catalyzed Epoxidation of Olefins with t-Butyl Hydroperoxide".
1411:
1078:
2181:
1258:
Kilty P. A.; Sachtler W. M. H. (1974). "The mechanism of the selective oxidation of ethylene to ethylene oxide".
422:
1544:
Sheldon R. A. (1980). "Synthetic and mechanistic aspects of metal-catalysed epoxidations with hydroperoxides".
1231:
Sajkowski, D. J.; Boudart, M. (1987). "Structure
Sensitivity of the Catalytic Oxidation of Ethene by Silver".
3011:
457:
502:
The reaction proceeds via what is commonly known as the "Butterfly
Mechanism". The peroxide is viewed as an
1035:
927:
1809:
1092:
442:
3140:
2584:
2174:
697:
693:
510:. The reaction is considered to be concerted. The butterfly mechanism allows ideal positioning of the
1385:
770:
2621:
689:
384:
2067:
890:
Epoxides undergo ring expansion reactions, illustrated by the insertion of carbon dioxide to give
3094:
480:
195:
152:, which are produced respectively on the scales of approximately 15 and 3 million tonnes/year.
805:, also known as polyethylene oxide. The reaction of an alcohol or a phenol with ethylene oxide,
684:
Epoxides are uncommon in nature. They arise usually via oxygenation of alkenes by the action of
2994:
993:
781:
epoxides through a simple nucleophilic addition of hydride (H); they produce the corresponding
640:
64:
56:
3101:
2989:
856:
584:
565:
396:
Simplified mechanism for metal-catalyzed epoxidation of alkenes with peroxide (ROOH) reagents
360:
167:
650:
3070:
2515:
2068:
2036:, Martha A. Umbreit (1981). "Deoxygenation of Epoxides with Lower Valent Tungsten Halides:
1046:
569:
2099:
Sasaki, Hiroshi (February 2007). "Curing properties of cycloaliphatic epoxy derivatives".
8:
2376:
898:
802:
782:
449:
2152:
2033:
1933:
1756:
1731:
1603:
1572:
1312:
1104:
522:
402:
133:
1613:
1517:
Berrisford, D. J.; Bolm, C.; Sharpless, K. B. (2003). "Ligand-Accelerated
Catalysis".
1370:
3135:
3060:
3030:
2788:
2410:
2144:
2073:
2015:
1953:
1912:
1815:
1784:
1761:
1675:
1649:
1577:
1557:
1461:
1407:
1192:
1157:
1108:
1073:
778:
774:
591:
514:
438:
380:
28:
1853:
1316:
576:, these reactions are useful for the enantioselective synthesis of chiral epoxides.
2765:
2259:
2197:
2136:
2112:
2108:
2081:
2050:
2007:
1980:
1945:
1904:
1881:
1751:
1743:
1710:
1641:
1585:
1553:
1526:
1437:
1366:
1339:
1302:
1294:
1267:
1240:
1215:
1184:
1149:
1100:
1061:
756:
658:
561:
104:
76:
40:
2156:
1645:
2984:
2743:
2738:
2721:
2704:
2505:
2254:
1620:
1031:
891:
707:
685:
673:
644:
620:, is prepared by the chlorohydrin method. It is a precursor in the production of
617:
573:
468:
383:
and alkyl hydroperoxides. Metal-catalyzed epoxidations were first explored using
149:
2011:
1949:
1931:
1670:
1483:
Paul D. Bartlett (1950). "Recent work on the mechanisms of peroxide reactions".
1456:
3055:
3050:
2926:
2921:
2916:
2709:
2676:
2460:
2442:
2432:
1023:
860:
798:
183:
145:
92:
1441:
1271:
1244:
3129:
3075:
3023:
2954:
2840:
2830:
2825:
2815:
2810:
2760:
2755:
2671:
2666:
2656:
2510:
2465:
2427:
2415:
2386:
2264:
2054:
1984:
1908:
1899:
Kosswig, Kurt (2002). "Surfactants". In Elvers, Barbara; et al. (eds.).
1873:
1219:
1188:
1153:
1012:
595:
472:
1428:[Oxidation of unsaturated compounds by means of organic peroxides].
657:
An intramolecular epoxide formation reaction is one of the key steps in the
3006:
2893:
2888:
2865:
2616:
2455:
2381:
2318:
2313:
2291:
2247:
2232:
2222:
2148:
2019:
1997:
1957:
1765:
1715:
1698:
1530:
1027:
806:
601:
503:
496:
418:
171:
1732:"Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis"
1141:
676:. In this reaction, a sulfonium is the leaving group instead of chloride.
3065:
3018:
2979:
2860:
2748:
2733:
2728:
2716:
2281:
2276:
2242:
2237:
2227:
2205:
2042:
1849:
1805:
1608:
997:
723:
711:
703:
621:
577:
507:
52:
2085:
1885:
1589:
1343:
2974:
2965:
2845:
2800:
2696:
2661:
2651:
2591:
2527:
2450:
2398:
1041:
The reaction of epoxides with amines is the basis for the formation of
958:
878:
845:
628:
588:
554:
453:
1747:
1307:
1298:
855:
reagents, with loss or retention of configuration. The combination of
405:
catalyzes the epoxidation at specifically less-substituted alkenes.
350:{\displaystyle {\ce {7 H2C=CH2 + 6 O2 -> 6 C2H4O + 2 CO2 + 2 H2O}}}
2941:
2855:
2820:
2805:
2793:
2636:
2611:
2420:
2032:
1426:"Oxydation ungesättigter Verbindungen mittels organischer Superoxyde"
852:
794:
744:
594:. It is used to prepare 2,3-epoxyalcohols from primary and secondary
434:
392:
364:
2166:
1425:
2949:
2903:
2870:
2566:
2472:
2346:
2301:
2286:
1870:
989:
943:
874:
719:
669:
613:
550:
546:
187:
156:
80:
60:
2140:
19:
2911:
2835:
2686:
2681:
2646:
2631:
2626:
2596:
2579:
2330:
2296:
1575:(1980). "The first practical method for asymmetric epoxidation".
715:
464:
119:
2125:
1811:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
1142:
Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides".
534:
The butterfly mechanism for the Prilezhaev epoxidation reaction.
379:
Metal complexes are useful catalysts for epoxidations involving
2999:
2931:
2775:
2484:
2477:
2371:
2352:
2341:
2325:
2271:
1454:
1404:
Advanced Organic Chemistry, Reactions, Mechanisms and Structure
867:
726:), the epoxides are often obtained in high enantioselectivity.
608:
198:
191:
160:
48:
44:
1284:
2880:
2850:
2783:
2641:
2606:
2601:
2574:
2522:
2489:
2393:
2217:
1854:"How to predict the regioselectivity of epoxide ring opening"
1803:
1042:
764:
580:
reagents may also be used to generate epoxides from alkenes.
414:
129:
124:
36:
1257:
1045:
glues and structural materials. A typical amine-hardener is
974:
3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate
734:
Ring-opening reactions dominate the reactivity of epoxides.
452:. This approach involves the oxidation of the alkene with a
155:
Aside from ethylene oxide, most epoxides are generated when
2308:
1814:(6th ed.), New York: Wiley-Interscience, p. 517,
1668:
1570:
368:
737:
1176:
1026:
is widely used to generate detergents and surfactants by
340:
320:
297:
284:
264:
244:
223:
1329:
374:
1636:
Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins".
1612:, Coll. Vol. 7, p. 461 (1990); Vol. 63, p. 66 (1985). (
1516:
428:
1781:
Medical Physiology: A Cellular And Molecular Approach
1423:
788:
207:
1095:. In Craver, Clara D.; Carraher, Charles E. (eds.).
1898:
1177:Siegfried Rebsdat; Dieter Mayer. "Ethylene Oxide".
897:An epoxide adjacent to an alcohol can undergo the
349:
16:Organic compounds with a carbon-carbon-oxygen ring
1970:
1631:
1629:
128:. However, few if any of the epoxy groups in the
3127:
1729:
1662:
1482:
1230:
840:
706:are intermediates in the oxidation of arenes by
186:industry generates its product from reaction of
1501:
1287:Industrial & Engineering Chemistry Research
1090:
692:which act as signalling molecules. and similar
371:catalysts can selectively epoxidize propylene.
1901:Ullmann's Encyclopedia of Industrial Chemistry
1638:Ullmann's Encyclopedia of Industrial Chemistry
1626:
1430:Berichte der Deutschen Chemischen Gesellschaft
1180:Ullmann's Encyclopedia of Industrial Chemistry
1145:Ullmann's Encyclopedia of Industrial Chemistry
1135:
1091:Massingill, J. L.; Bauer, R. S. (2000-01-01).
759:in asymmetric epoxides generally follows the S
560:Hydroperoxides are also employed in catalytic
2182:
1836:Organic Synthesis: the disconnection approach
1772:
1543:
1015:exists in equilibrium with the oxepin isomer.
748:Two pathways for the hydrolysis of an epoxide
363:. Other alkenes fail to react usefully, even
51:. This triangular structure has substantial
649:
609:Dehydrohalogenation and other γ eliminations
600:
122:formed from epoxide precursors is called an
2092:
1892:
1833:
1696:
1564:
1356:
930:is a component in common household "epoxy".
837:With anhydrides, epoxides give polyesters.
408:
159:reagents donate a single oxygen atom to an
2189:
2175:
1506:. Interscience, New York. pp. 67–106.
1448:
1359:Journal of Molecular Catalysis A: Chemical
1260:Catalysis Reviews: Science and Engineering
540:
1755:
1714:
1635:
1306:
809:, is widely used to produce surfactants:
448:Typical laboratory operations employ the
359:Only ethylene produces an epoxide during
329:
309:
273:
253:
212:
1455:Harold Hibbert and Pauline Burt (1941).
743:
612:
391:
18:
848:cleaves the ring to β-lithioalkoxides.
738:Hydrolysis and addition of nucleophiles
144:The dominant epoxides industrially are
3128:
2129:Environmental Toxicology and Chemistry
2098:
1669:Koppenhoefer, B.; Schurig, V. (1993).
1099:. Oxford: Pergamon. pp. 393–424.
1038:of medical instruments and materials.
942:The chemical structure of the epoxide
2196:
2170:
1848:
1778:
1537:
1396:
1383:
1097:Applied Polymer Science: 21st Century
767:glues and the production of glycols.
463:. Illustrative is the epoxidation of
375:Organic peroxides and metal catalysts
177:
39:, where the ether forms a three-atom
1834:Warren, Stuart; Wyatt, Paul (2008).
1323:
1251:
1210:
1208:
1064:, making many of them highly toxic.
429:Transfer from peroxycarboxylic acids
413:Electron-deficient olefins, such as
851:Epoxides can be deoxygenated using
13:
1932:Julie M. Longo; Maria J. Sanford;
1838:(2nd ed.). Wiley. p. 39.
1783:. Elsevier/Saunders. p. 108.
1084:
884:
789:Polymerization and oligomerization
529:
75:A compound containing the epoxide
14:
3152:
1406:. 3rd ed. John Wiley & Sons.
1205:
996:(ESBO), a commercially important
961:are naturally occurring epoxides.
946:, a common chemical intermediate.
793:Polymerization of epoxides gives
666:Johnson–Corey–Chaykovsky reaction
1386:"Selective reactions of Alkenes"
1105:10.1016/b978-008043417-9/50023-4
1005:
981:
966:
951:
935:
920:
688:. (but see also the short-lived
643:, most of the world's supply of
479:
2119:
2061:
2026:
1991:
1964:
1925:
1864:
1842:
1827:
1797:
1723:
1690:
1596:
1510:
1495:
1476:
1417:
1384:Taber, Douglass (25 Sep 2006).
679:
587:reaction is one of the premier
423:nucleophilic conjugate addition
70:
2113:10.1016/j.porgcoat.2006.09.030
1546:Journal of Molecular Catalysis
1424:Nikolaus Prileschajew (1909).
1377:
1350:
1278:
1224:
1170:
267:
1:
1646:10.1002/14356007.a09_547.pub2
1371:10.1016/S1381-1169(96)00291-9
1128:
841:Metallation and deoxygenation
2101:Progress in Organic Coatings
1903:. Weinheim, GER: Wiley-VCH.
1558:10.1016/0304-5102(80)85010-3
1504:Peroxide Reaction Mechanisms
1390:Organic Chemistry Highlights
928:Bisphenol A diglycidyl ether
729:
668:epoxides are generated from
445:, but are more explosive.
139:
7:
2012:10.1021/acs.orglett.5b01583
1950:10.1021/acs.chemrev.6b00553
1606:; Exon, C. M.; Regenye, R.
1485:Record of Chemical Progress
1067:
698:epoxyeicosatetraenoic acids
694:epoxydocosapentaenoic acids
111:, which can also be called
10:
3157:
1685:, vol. 8, p. 434
1519:Angew. Chem. Int. Ed. Engl
1471:, vol. 1, p. 494
877:, epoxides convert to the
564:epoxidations, such as the
523:coarctate transition state
3084:
3043:
2963:
2940:
2902:
2879:
2774:
2695:
2565:
2542:
2498:
2441:
2364:
2339:
2204:
1730:Thibodeaux C. J. (2012).
1442:10.1002/cber.190904204100
1272:10.1080/01614947408079624
1245:10.1080/01614948708078611
1079:Juliá–Colonna epoxidation
1055:
1030:. Its hydrolysis affords
771:Lithium aluminium hydride
690:epoxyeicosatrienoic acids
647:arises via this route.
55:, making epoxides highly
2055:10.15227/orgsyn.060.0029
1985:10.15227/orgsyn.072.0173
1909:10.1002/14356007.a25_747
1502:John O. Edwards (1962).
1220:10.1002/14356007.a22_239
1189:10.1002/14356007.a10_117
1154:10.1002/14356007.a09_531
976:, precursor to coatings.
710:. For prochiral arenes (
409:Nucleophilic epoxidation
385:tert-butyl hydroperoxide
367:, though TS-1 supported
3095:chemical classification
1183:. Weinheim: Wiley-VCH.
1148:. Weinheim: Wiley-VCH.
992:, a major component of
905:
541:Asymmetric epoxidations
1858:Chemistry with a twist
1716:10.19261/cjm.2023.1083
1531:10.1002/anie.199510591
1034:. It is also used for
994:epoxidized soybean oil
749:
654:
641:propylene chlorohydrin
625:
605:
535:
397:
351:
24:
3102:chemical nomenclature
912:Illustrative epoxides
857:tungsten hexachloride
747:
653:
616:
604:
585:Sharpless epoxidation
566:Sharpless epoxidation
533:
395:
361:incomplete combustion
352:
168:t-butyl hydroperoxide
107:, as in the compound
22:
1697:Silva, P.J. (2023).
1402:March, Jerry. 1985.
1047:triethylenetetramine
801:polymerizes to give
572:. Together with the
570:Jacobsen epoxidation
205:
2558:not C, H or O)
2086:10.1021/ja00773a045
1944:(24): 15167–15197.
1886:10.1021/jo01278a005
1804:Smith, Michael B.;
1590:10.1021/ja00538a077
1344:10.1021/jo01017a520
899:Payne rearrangement
803:polyethylene glycol
506:, and the alkene a
450:Prilezhaev reaction
342:
322:
299:
286:
266:
246:
225:
3000:Hypervalent iodine
2069:K. Barry Sharpless
2034:K. Barry Sharpless
1934:Geoffrey W. Coates
1619:2013-09-27 at the
873:When treated with
750:
655:
626:
606:
592:chemical reactions
536:
515:sigma star orbital
403:Vanadium(II) oxide
398:
347:
330:
310:
287:
274:
254:
234:
213:
178:Ethylene oxidation
25:
3141:Functional groups
3123:
3122:
3061:Sulfenyl chloride
3039:
3038:
2538:
2537:
2357:(only C, H and O)
2198:Functional groups
2080:(18): 6538–6540.
2074:J. Am. Chem. Soc.
2040:-Cyclododecene".
1852:(28 April 2013).
1821:978-0-471-72091-1
1790:978-1-4160-2328-9
1779:Boron WF (2003).
1748:10.1021/cr200073d
1683:Collected Volumes
1676:Organic Syntheses
1584:(18): 5974–5976.
1578:J. Am. Chem. Soc.
1525:(10): 1059–1070.
1469:Collected Volumes
1462:Organic Syntheses
1299:10.1021/ie0513090
1293:(10): 3447–3459.
1233:Catalysis Reviews
1114:978-0-08-043417-9
1074:Epoxide hydrolase
1062:alkylating agents
892:cyclic carbonates
775:aluminium hydride
443:perform similarly
439:dimethyldioxirane
419:acryl derivatives
381:hydrogen peroxide
345:
333:
313:
302:
290:
277:
257:
237:
228:
216:
113:1,2-heptene oxide
29:organic chemistry
23:A generic epoxide
3148:
3090:
2995:Trifluoromethoxy
2563:
2562:
2559:
2362:
2361:
2358:
2211:
2191:
2184:
2177:
2168:
2167:
2161:
2160:
2123:
2117:
2116:
2107:(2–3): 227–230.
2096:
2090:
2089:
2065:
2059:
2058:
2030:
2024:
2023:
1995:
1989:
1988:
1968:
1962:
1961:
1929:
1923:
1922:
1896:
1890:
1889:
1868:
1862:
1861:
1846:
1840:
1839:
1831:
1825:
1824:
1801:
1795:
1794:
1776:
1770:
1769:
1759:
1742:(3): 1681–1709.
1727:
1721:
1720:
1718:
1694:
1688:
1686:
1679:
1666:
1660:
1659:
1633:
1624:
1604:Sharpless, K. B.
1600:
1594:
1593:
1573:Sharpless, K. B.
1568:
1562:
1561:
1541:
1535:
1534:
1514:
1508:
1507:
1499:
1493:
1492:
1480:
1474:
1472:
1465:
1452:
1446:
1445:
1436:(4): 4811–4815.
1421:
1415:
1400:
1394:
1393:
1381:
1375:
1374:
1354:
1348:
1347:
1327:
1321:
1320:
1310:
1282:
1276:
1275:
1255:
1249:
1248:
1228:
1222:
1212:
1203:
1202:
1174:
1168:
1167:
1139:
1124:
1122:
1121:
1009:
985:
970:
955:
939:
924:
757:regioselectivity
674:sulfonium ylides
659:Darzens reaction
596:allylic alcohols
589:enantioselective
562:enantioselective
520:
513:
483:
356:
354:
353:
348:
346:
343:
341:
338:
331:
321:
318:
311:
300:
298:
295:
288:
285:
282:
275:
265:
262:
255:
245:
242:
235:
233:
226:
224:
221:
214:
109:1,2-epoxyheptane
105:functional group
77:functional group
47:and one atom of
3156:
3155:
3151:
3150:
3149:
3147:
3146:
3145:
3126:
3125:
3124:
3119:
3088:
3080:
3035:
2990:Trichloromethyl
2985:Trifluoromethyl
2959:
2936:
2898:
2875:
2770:
2739:Phosphine oxide
2691:
2557:
2555:
2554:
2552:
2550:
2548:
2546:
2544:
2534:
2494:
2437:
2356:
2355:
2350:
2345:
2335:
2209:
2208:
2200:
2195:
2165:
2164:
2124:
2120:
2097:
2093:
2066:
2062:
2031:
2027:
1996:
1992:
1969:
1965:
1930:
1926:
1919:
1897:
1893:
1869:
1865:
1847:
1843:
1832:
1828:
1822:
1802:
1798:
1791:
1777:
1773:
1728:
1724:
1695:
1691:
1681:
1667:
1663:
1656:
1634:
1627:
1621:Wayback Machine
1601:
1597:
1569:
1565:
1542:
1538:
1515:
1511:
1500:
1496:
1481:
1477:
1467:
1457:"Styrene Oxide"
1453:
1449:
1422:
1418:
1401:
1397:
1382:
1378:
1355:
1351:
1328:
1324:
1283:
1279:
1256:
1252:
1229:
1225:
1213:
1206:
1199:
1175:
1171:
1164:
1140:
1136:
1131:
1119:
1117:
1115:
1087:
1085:Further reading
1070:
1058:
1052:
1032:ethylene glycol
1021:
1020:
1019:
1016:
1010:
1001:
986:
977:
971:
962:
956:
947:
940:
931:
925:
914:
913:
908:
887:
885:Other reactions
843:
832:
828:
824:
820:
816:
791:
762:
740:
732:
708:cytochrome P450
686:cytochrome P450
682:
645:propylene oxide
618:Epichlorohydrin
611:
574:Shi epoxidation
543:
518:
511:
469:perbenzoic acid
437:reagents (e.g.
431:
411:
377:
339:
334:
319:
314:
296:
291:
283:
278:
263:
258:
243:
238:
229:
222:
217:
208:
206:
203:
202:
180:
150:propylene oxide
142:
102:
98:
90:
86:
73:
43:: two atoms of
17:
12:
11:
5:
3154:
3144:
3143:
3138:
3121:
3120:
3118:
3117:
3116:
3115:
3110:
3098:
3091:
3085:
3082:
3081:
3079:
3078:
3076:Sulfinylamines
3073:
3068:
3063:
3058:
3056:Phosphoramides
3053:
3051:Isothiocyanate
3047:
3045:
3041:
3040:
3037:
3036:
3034:
3033:
3028:
3027:
3026:
3016:
3015:
3014:
3004:
3003:
3002:
2997:
2992:
2987:
2982:
2971:
2969:
2961:
2960:
2958:
2957:
2952:
2946:
2944:
2938:
2937:
2935:
2934:
2929:
2927:Selenenic acid
2924:
2922:Seleninic acid
2919:
2917:Selenonic acid
2914:
2908:
2906:
2900:
2899:
2897:
2896:
2891:
2885:
2883:
2877:
2876:
2874:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2797:
2796:
2786:
2780:
2778:
2772:
2771:
2769:
2768:
2763:
2758:
2753:
2752:
2751:
2741:
2736:
2731:
2726:
2725:
2724:
2714:
2713:
2712:
2710:Phosphodiester
2701:
2699:
2693:
2692:
2690:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2594:
2589:
2588:
2587:
2582:
2571:
2569:
2560:
2556:(one element,
2540:
2539:
2536:
2535:
2533:
2532:
2531:
2530:
2520:
2519:
2518:
2513:
2502:
2500:
2496:
2495:
2493:
2492:
2487:
2482:
2481:
2480:
2470:
2469:
2468:
2463:
2458:
2447:
2445:
2439:
2438:
2436:
2435:
2433:Methylenedioxy
2430:
2425:
2424:
2423:
2418:
2408:
2407:
2406:
2401:
2391:
2390:
2389:
2379:
2374:
2368:
2366:
2359:
2337:
2336:
2334:
2333:
2328:
2323:
2322:
2321:
2316:
2306:
2305:
2304:
2299:
2294:
2289:
2284:
2279:
2269:
2268:
2267:
2262:
2252:
2251:
2250:
2245:
2240:
2235:
2230:
2225:
2214:
2212:
2210:(only C and H)
2202:
2201:
2194:
2193:
2186:
2179:
2171:
2163:
2162:
2135:(3): 697–704.
2118:
2091:
2060:
2025:
2006:(13): 3346–9.
1990:
1963:
1924:
1918:978-3527306732
1917:
1891:
1880:(3): 537–539.
1863:
1841:
1826:
1820:
1796:
1789:
1771:
1722:
1689:
1661:
1655:978-3527306732
1654:
1625:
1595:
1563:
1536:
1509:
1494:
1475:
1447:
1416:
1395:
1376:
1349:
1322:
1277:
1250:
1239:(4): 325–360.
1223:
1204:
1198:978-3527306732
1197:
1169:
1163:978-3527306732
1162:
1133:
1132:
1130:
1127:
1126:
1125:
1113:
1093:"Epoxy Resins"
1086:
1083:
1082:
1081:
1076:
1069:
1066:
1057:
1054:
1024:Ethylene oxide
1018:
1017:
1011:
1004:
1002:
987:
980:
978:
972:
965:
963:
957:
950:
948:
941:
934:
932:
926:
919:
916:
915:
911:
910:
909:
907:
904:
903:
902:
895:
886:
883:
842:
839:
835:
834:
830:
826:
822:
818:
814:
799:ethylene oxide
797:. For example
790:
787:
760:
752:
751:
739:
736:
731:
728:
681:
678:
639:Starting with
610:
607:
542:
539:
538:
537:
485:
484:
430:
427:
410:
407:
400:
399:
376:
373:
337:
328:
325:
317:
308:
305:
294:
281:
272:
269:
261:
252:
249:
241:
232:
220:
211:
184:ethylene oxide
179:
176:
146:ethylene oxide
141:
138:
134:curing process
100:
96:
93:ethylene oxide
88:
84:
72:
69:
15:
9:
6:
4:
3:
2:
3153:
3142:
3139:
3137:
3134:
3133:
3131:
3114:
3111:
3109:
3106:
3105:
3104:
3103:
3099:
3097:
3096:
3092:
3087:
3086:
3083:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3057:
3054:
3052:
3049:
3048:
3046:
3042:
3032:
3029:
3025:
3022:
3021:
3020:
3017:
3013:
3010:
3009:
3008:
3005:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2977:
2976:
2973:
2972:
2970:
2968:
2967:
2962:
2956:
2955:Telluroketone
2953:
2951:
2948:
2947:
2945:
2943:
2939:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2909:
2907:
2905:
2901:
2895:
2892:
2890:
2887:
2886:
2884:
2882:
2878:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2841:Sulfonic acid
2839:
2837:
2834:
2832:
2831:Sulfinic acid
2829:
2827:
2826:Thiosulfonate
2824:
2822:
2819:
2817:
2816:Thiosulfinate
2814:
2812:
2811:Sulfenic acid
2809:
2807:
2804:
2802:
2799:
2795:
2792:
2791:
2790:
2787:
2785:
2782:
2781:
2779:
2777:
2773:
2767:
2766:Phosphaallene
2764:
2762:
2761:Phosphaalkyne
2759:
2757:
2756:Phosphaalkene
2754:
2750:
2747:
2746:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2723:
2720:
2719:
2718:
2715:
2711:
2708:
2707:
2706:
2703:
2702:
2700:
2698:
2694:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2586:
2583:
2581:
2578:
2577:
2576:
2573:
2572:
2570:
2568:
2564:
2561:
2541:
2529:
2526:
2525:
2524:
2521:
2517:
2514:
2512:
2509:
2508:
2507:
2504:
2503:
2501:
2497:
2491:
2488:
2486:
2483:
2479:
2476:
2475:
2474:
2471:
2467:
2464:
2462:
2459:
2457:
2454:
2453:
2452:
2449:
2448:
2446:
2444:
2440:
2434:
2431:
2429:
2428:Ethylenedioxy
2426:
2422:
2419:
2417:
2414:
2413:
2412:
2409:
2405:
2402:
2400:
2397:
2396:
2395:
2392:
2388:
2385:
2384:
2383:
2380:
2378:
2375:
2373:
2370:
2369:
2367:
2363:
2360:
2354:
2348:
2343:
2338:
2332:
2329:
2327:
2324:
2320:
2317:
2315:
2312:
2311:
2310:
2307:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2274:
2273:
2270:
2266:
2263:
2261:
2258:
2257:
2256:
2253:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2220:
2219:
2216:
2215:
2213:
2207:
2203:
2199:
2192:
2187:
2185:
2180:
2178:
2173:
2172:
2169:
2158:
2154:
2150:
2146:
2142:
2141:10.1897/03-83
2138:
2134:
2130:
2122:
2114:
2110:
2106:
2102:
2095:
2087:
2083:
2079:
2076:
2075:
2070:
2064:
2056:
2052:
2048:
2045:
2044:
2039:
2035:
2029:
2021:
2017:
2013:
2009:
2005:
2001:
1994:
1986:
1982:
1978:
1974:
1967:
1959:
1955:
1951:
1947:
1943:
1939:
1935:
1928:
1920:
1914:
1910:
1906:
1902:
1895:
1887:
1883:
1879:
1876:
1875:
1874:J. Org. Chem.
1867:
1859:
1855:
1851:
1845:
1837:
1830:
1823:
1817:
1813:
1812:
1807:
1800:
1792:
1786:
1782:
1775:
1767:
1763:
1758:
1753:
1749:
1745:
1741:
1737:
1733:
1726:
1717:
1712:
1708:
1704:
1703:Chem. J. Mold
1700:
1693:
1684:
1678:
1677:
1672:
1665:
1657:
1651:
1647:
1643:
1640:. Wiley-VCH.
1639:
1632:
1630:
1622:
1618:
1615:
1611:
1610:
1605:
1602:Hill, J. G.;
1599:
1591:
1587:
1583:
1580:
1579:
1574:
1571:Katsuki, T.;
1567:
1559:
1555:
1551:
1547:
1540:
1532:
1528:
1524:
1520:
1513:
1505:
1498:
1490:
1486:
1479:
1470:
1464:
1463:
1458:
1451:
1443:
1439:
1435:
1432:(in German).
1431:
1427:
1420:
1413:
1412:0-471-85472-7
1409:
1405:
1399:
1391:
1387:
1380:
1372:
1368:
1364:
1360:
1353:
1345:
1341:
1337:
1333:
1326:
1318:
1314:
1309:
1304:
1300:
1296:
1292:
1288:
1281:
1273:
1269:
1265:
1261:
1254:
1246:
1242:
1238:
1234:
1227:
1221:
1217:
1211:
1209:
1200:
1194:
1190:
1186:
1182:
1181:
1173:
1165:
1159:
1155:
1151:
1147:
1146:
1138:
1134:
1116:
1110:
1106:
1102:
1098:
1094:
1089:
1088:
1080:
1077:
1075:
1072:
1071:
1065:
1063:
1060:Epoxides are
1053:
1050:
1048:
1044:
1039:
1037:
1036:sterilisation
1033:
1029:
1025:
1014:
1013:Benzene oxide
1008:
1003:
999:
995:
991:
984:
979:
975:
969:
964:
960:
954:
949:
945:
938:
933:
929:
923:
918:
917:
900:
896:
893:
889:
888:
882:
881:(thiiranes).
880:
876:
871:
869:
865:
864:-butyllithium
863:
858:
854:
849:
847:
838:
812:
811:
810:
808:
804:
800:
796:
786:
784:
780:
776:
772:
768:
766:
758:
746:
742:
741:
735:
727:
725:
721:
717:
713:
709:
705:
701:
699:
695:
691:
687:
677:
675:
671:
667:
662:
660:
652:
648:
646:
642:
637:
633:
630:
623:
619:
615:
603:
599:
597:
593:
590:
586:
581:
579:
575:
571:
567:
563:
558:
556:
552:
548:
532:
528:
527:
526:
524:
516:
509:
505:
500:
498:
497:diastereomers
494:
490:
482:
478:
477:
476:
474:
473:styrene oxide
470:
466:
462:
460:
455:
451:
446:
444:
440:
436:
426:
424:
420:
416:
406:
404:
394:
390:
389:
388:
386:
382:
372:
370:
366:
362:
357:
335:
326:
323:
315:
306:
303:
292:
279:
270:
259:
250:
247:
239:
230:
218:
209:
200:
197:
196:heterogeneous
193:
189:
185:
175:
173:
169:
164:
162:
158:
153:
151:
147:
137:
135:
131:
127:
126:
121:
116:
114:
110:
106:
94:
82:
78:
68:
66:
62:
58:
54:
50:
46:
42:
38:
34:
30:
21:
3100:
3093:
3007:Vinyl halide
2964:
2894:Borinic acid
2889:Boronic acid
2866:Thioxanthate
2403:
2206:Hydrocarbons
2132:
2128:
2121:
2104:
2100:
2094:
2077:
2072:
2063:
2046:
2041:
2037:
2028:
2003:
1999:
1993:
1976:
1972:
1966:
1941:
1937:
1927:
1900:
1894:
1877:
1872:
1866:
1857:
1850:Rzepa, Henry
1844:
1835:
1829:
1810:
1806:March, Jerry
1799:
1780:
1774:
1739:
1735:
1725:
1709:(2): 87–95.
1706:
1702:
1692:
1682:
1674:
1664:
1637:
1607:
1598:
1581:
1576:
1566:
1549:
1545:
1539:
1522:
1518:
1512:
1503:
1497:
1488:
1484:
1478:
1468:
1460:
1450:
1433:
1429:
1419:
1403:
1398:
1389:
1379:
1362:
1358:
1352:
1335:
1332:J. Org. Chem
1331:
1325:
1290:
1286:
1280:
1263:
1259:
1253:
1236:
1232:
1226:
1178:
1172:
1143:
1137:
1118:. Retrieved
1096:
1059:
1051:
1040:
1028:ethoxylation
1022:
872:
861:
850:
844:
836:
821:O → R(OC
807:ethoxylation
792:
769:
753:
733:
704:Arene oxides
702:
683:
680:Biosynthesis
663:
656:
638:
634:
627:
622:epoxy resins
582:
559:
544:
504:electrophile
501:
492:
488:
486:
458:
447:
432:
412:
401:
378:
358:
181:
172:ethylbenzene
165:
154:
143:
132:survive the
123:
117:
112:
108:
74:
71:Nomenclature
63:, and often
35:is a cyclic
32:
26:
3071:Thiocyanate
3066:Sulfonamide
3031:Perchlorate
3019:Acyl halide
2980:Fluoroethyl
2861:Thionoester
2749:Phosphonium
2734:Phosphinate
2729:Phosphonous
2717:Phosphonate
2416:Hydroperoxy
2238:Cyclopropyl
2043:Org. Synth.
1609:Org. Synth.
1552:: 107–206.
1365:: 449–454.
1338:(6): 2074.
998:plasticizer
988:Epoxidized
959:Epothilones
813:ROH + n C
724:benzopyrene
712:naphthalene
672:groups and
629:Halohydrins
578:Oxaziridine
508:nucleophile
194:. Modified
157:peroxidized
53:ring strain
3130:Categories
2975:Haloalkane
2846:Thioketone
2801:Persulfide
2697:Phosphorus
2662:Isocyanate
2652:Isonitrile
2553:or oxygen
2551:hydrogen,
2547:not being
2528:Orthoester
2421:Dioxiranes
2399:Enol ether
2287:1-Propenyl
1973:Org. Synth
1308:1874/20149
1129:References
1120:2023-12-20
879:episulfide
866:gives the
846:Lithiation
795:polyethers
555:molybdenum
454:peroxyacid
3108:inorganic
2942:Tellurium
2856:Thioester
2821:Sulfoxide
2806:Disulfide
2794:Sulfonium
2744:Phosphine
2722:Phosphite
2705:Phosphate
2637:Carbamate
2612:Hydrazone
2545:element,
2543:Only one
2516:Anhydride
2255:Methylene
2000:Org. Lett
1938:Chem. Rev
1736:Chem. Rev
853:oxophilic
730:Reactions
720:benzoates
435:dioxirane
365:propylene
268:⟶
140:Synthesis
3136:Epoxides
3089:See also
3024:Chloride
2950:Tellurol
2904:Selenium
2871:Xanthate
2585:Ammonium
2567:Nitrogen
2549:carbon,
2506:Carboxyl
2473:Aldehyde
2461:Acryloyl
2443:carbonyl
2347:hydrogen
2302:Cumulene
2149:15285364
2020:26065934
1958:27936619
1808:(2007),
1766:22017381
1617:Archived
1491:: 47–51.
1317:94240406
1266:: 1–16.
1068:See also
1049:(TETA).
990:linolein
944:glycidol
901:in base.
875:thiourea
670:carbonyl
568:and the
551:vanadium
547:titanium
495:epoxide
456:such as
188:ethylene
81:ethylene
65:volatile
61:nonpolar
57:reactive
3113:organic
2912:Selenol
2836:Sulfone
2789:Sulfide
2687:NONOate
2682:Nitroso
2672:Nitrite
2667:Nitrate
2657:Cyanate
2647:Nitrile
2632:Amidine
2627:Imidate
2597:Nitrene
2592:Hydrazo
2580:Enamine
2511:Acetoxy
2499:carboxy
2466:Benzoyl
2404:Epoxide
2387:Methoxy
2377:Alcohol
2331:Carbene
2265:Methine
1979:: 173.
1757:3288687
1614:Article
783:alcohol
716:toluene
664:In the
491:and/or
465:styrene
120:polymer
33:epoxide
3012:Iodide
2932:Selone
2776:Sulfur
2485:Ketone
2478:Ketene
2456:Acetyl
2411:Peroxy
2382:Alkoxy
2372:Acetal
2353:oxygen
2342:carbon
2326:Alkyne
2319:Benzyl
2314:Phenyl
2297:Allene
2292:Crotyl
2272:Alkene
2260:Bridge
2248:Pentyl
2233:Propyl
2223:Methyl
2157:847639
2155:
2147:
2049:: 29.
2018:
1956:
1915:
1818:
1787:
1764:
1754:
1652:
1410:
1315:
1195:
1160:
1111:
1056:Safety
868:alkene
779:reduce
696:, and
553:, and
415:enones
199:silver
192:oxygen
161:alkene
49:oxygen
45:carbon
3044:Other
2881:Boron
2851:Thial
2784:Thiol
2677:Nitro
2642:Imide
2622:Amide
2607:Oxime
2602:Imine
2575:Amine
2523:Ester
2490:Ynone
2394:Ether
2365:R-O-R
2340:Only
2282:Allyl
2277:Vinyl
2243:Butyl
2228:Ethyl
2218:Alkyl
2153:S2CID
2038:trans
1313:S2CID
1043:epoxy
777:both
765:epoxy
493:trans
467:with
166:Both
130:resin
125:epoxy
91:) is
37:ether
31:, an
2966:Halo
2451:Acyl
2351:and
2309:Aryl
2145:PMID
2016:PMID
1954:PMID
1913:ISBN
1816:ISBN
1785:ISBN
1762:PMID
1650:ISBN
1408:ISBN
1193:ISBN
1158:ISBN
1109:ISBN
906:Uses
859:and
598:.
583:The
517:for
461:CPBA
417:and
190:and
182:The
170:and
148:and
41:ring
2617:Azo
2137:doi
2109:doi
2082:doi
2051:doi
2008:doi
1981:doi
1946:doi
1942:116
1905:doi
1882:doi
1752:PMC
1744:doi
1740:112
1711:doi
1642:doi
1586:doi
1582:102
1554:doi
1527:doi
1438:doi
1367:doi
1363:117
1340:doi
1303:hdl
1295:doi
1268:doi
1241:doi
1216:doi
1185:doi
1150:doi
1101:doi
773:or
700:.)
519:C−C
512:O−O
489:cis
471:to
27:In
3132::
2349:,
2344:,
2151:.
2143:.
2133:23
2131:.
2105:58
2103:.
2078:94
2047:60
2014:.
2004:17
2002:.
1977:72
1975:.
1952:.
1940:.
1911:.
1878:32
1856:.
1760:.
1750:.
1738:.
1734:.
1707:18
1705:.
1701:.
1680:;
1673:.
1648:.
1628:^
1548:.
1523:95
1521:.
1489:11
1487:.
1466:;
1459:.
1434:42
1388:.
1361:.
1336:30
1334:.
1311:.
1301:.
1291:45
1289:.
1264:10
1262:.
1237:29
1235:.
1207:^
1191:.
1156:.
1107:.
870:.
833:OH
785:.
722:,
718:,
714:,
661:.
557:.
549:,
525:.
475::
441:)
369:Au
312:CO
236:CH
136:.
118:A
115:.
95:(C
83:(C
67:.
2190:e
2183:t
2176:v
2159:.
2139::
2115:.
2111::
2088:.
2084::
2057:.
2053::
2022:.
2010::
1987:.
1983::
1960:.
1948::
1921:.
1907::
1888:.
1884::
1860:.
1793:.
1768:.
1746::
1719:.
1713::
1687:.
1658:.
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1592:.
1588::
1560:.
1556::
1550:1
1533:.
1529::
1473:.
1444:.
1440::
1414:.
1392:.
1373:.
1369::
1346:.
1342::
1319:.
1305::
1297::
1274:.
1270::
1247:.
1243::
1218::
1201:.
1187::
1166:.
1152::
1123:.
1103::
1000:.
894:.
862:n
831:n
829:)
827:4
825:H
823:2
819:4
817:H
815:2
761:N
624:.
459:m
344:O
336:2
332:H
327:2
324:+
316:2
307:2
304:+
301:O
293:4
289:H
280:2
276:C
271:6
260:2
256:O
251:6
248:+
240:2
231:=
227:C
219:2
215:H
210:7
101:4
99:H
97:2
89:4
87:H
85:2
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