544:
20:
369:
802:
477:
431:
630:
Many industrial peroxides are produced using hydrogen peroxide. Reactions with aldehydes and ketones yield a series of compounds depending on conditions. Specific reactions include addition of hydrogen peroxide across the C=O double bond:
584:
Although ether hydroperoxide often form adventitiously (i.e. autoxidation), they can be prepared in high yield by the acid-catalyzed addition of hydrogen peroxide to vinyl ethers:
299:
This reaction is the basis of methods for analysis of organic peroxides. Another way to evaluate the content of peracids and peroxides is the volumetric titration with
381:
Hydroperoxides are intermediates in the production of many organic compounds in industry. For example, the cobalt catalyzed oxidation of cyclohexane to
1083:
936:
836:
969:
Higuchi, T.; Zuck, Donald Anton (1951). "Behaviors of
Several Compounds as Indicators in Lithium Aluminum Hydride Titration of Functional Groups".
798:
Many hydroperoxides are derived from fatty acids, steroids, and terpenes. The biosynthesis of these species is affected extensively by enzymes.
577:. Such compounds can result in a serious explosion when distilled. To minimize this problem, commercial samples of THF are often inhibited with
343:"The single most important synthetic application of alkyl hydroperoxides is without doubt the metal-catalysed epoxidation of alkenes." In the
1284:
1215:
Bryant E. Rossiter and
Michael O. Frederick "Triphenylmethyl Hydroperoxide" E-EROS Encyclopedia of Reagents for Organic Synthesis, 2013.
1189:
Milas, Nicholas A.; Peeler, Robert L.; Mageli, Orville L. (1954). "Organic
Peroxides. XIX. α-Hydroperoxyethers and Related Peroxides".
446:
C−H bonds are especially susceptible to oxygenation. Such reactivity is exploited industrially on a large scale for the production of
2203:
2208:
466:
that reacts with oxygen to form an intermediate that abstracts a hydrogen atom from a weak C-H bond. The resulting radical binds
23:
The general structure of an organic hydroperoxide with the blue marked functional group, where R stands for any group, typically
869:
Bach, Robert D.; Ayala, Philippe Y.; Schlegel, H. B. (1996). "A Reassessment of the Bond
Dissociation Energies of Peroxides. An
918:
508:
with a hydrocarbon. Autoxidation is a radical reaction that begins with the abstraction of an H atom from a relatively weak
1053:; Exon, C. M.; Regenye, R. (1985). "Enantioselective Epoxidation Of Allylic Alcohols: (2s,3s)-3-propyloxiranemethanol".
1100:
953:
853:
1176:
1152:
77:, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive
1277:
2107:
581:(BHT). Distillation of THF to dryness is avoided because the explosive peroxides concentrate in the residue.
368:
996:
Martin, A. J. (1957). "Potentiometric titration of hydroperoxide and peracid in
Anhydrous Ethylenediamine".
901:
Otto Exner (1983). "Stereochemical and conformational aspects of peroxy compounds". In Saul Patai (ed.).
2246:
2236:
2231:
1680:
1270:
521:
312:
274:
1717:
578:
513:
347:
158:
132:
2241:
2190:
934:
Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried. "Peroxy
Compounds, Organic".
834:
Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried. "Peroxy
Compounds, Organic".
2090:
574:
2197:
2085:
1232:
Matsui K (2006). "Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism".
362:
2166:
1611:
517:
481:
459:
245:
216:
186:
69:(•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called
782:
Triphenylmethanol reacts with hydrogen peroxide gives the unusually stable hydroperoxide,
8:
1472:
270:
1050:
422:, as found in many paints and varnishes, function via the formation of hydroperoxides.
173:
2156:
2126:
1884:
1506:
1249:
1172:
1148:
1096:
949:
914:
875:
849:
562:
543:
473:, to give hydroperoxyl (ROO•), which then continues the cycle of H-atom abstraction.
463:
38:
19:
1861:
1355:
1293:
1241:
1220:
1216:
1198:
1145:
Reaktionsmechanismen: organische
Reaktionen, Stereochemie, moderne Synthesemethoden
1125:
1088:
1063:
1031:
1005:
978:
941:
906:
883:
841:
82:
74:
62:
46:
42:
24:
2080:
1839:
1834:
1817:
1800:
1601:
1350:
1048:
566:
351:
308:
304:
2151:
2146:
2022:
2017:
2012:
1805:
1772:
1556:
1538:
1528:
810:
550:
451:
344:
124:
78:
1245:
1035:
910:
135:
of 45–50 kcal/mol (190–210 kJ/mol), less than half the strengths of
2225:
2171:
2119:
2050:
1936:
1926:
1921:
1911:
1906:
1856:
1851:
1767:
1762:
1752:
1606:
1561:
1523:
1482:
1360:
1129:
1092:
1067:
945:
845:
806:
558:
382:
224:
165:
101:
2102:
1989:
1984:
1961:
1712:
1551:
1477:
1414:
1409:
1387:
1343:
1328:
1318:
1253:
814:
498:
66:
2161:
2114:
2075:
1956:
1844:
1829:
1824:
1812:
1377:
1372:
1338:
1333:
1323:
1301:
1055:
805:
Illustrative biosynthetic transformation involving a hydroperoxide. Here
570:
97:
1202:
1009:
982:
703:
Addition of this initial adduct to a second equivalent of the carbonyl:
657:
In some cases, these hydroperoxides convert to give cyclic diperoxides:
2070:
2061:
1941:
1896:
1792:
1757:
1747:
1687:
1623:
1546:
1494:
419:
887:
2037:
1951:
1916:
1901:
1889:
1732:
1707:
1516:
801:
497:
The most important (in a commercial sense) peroxides are produced by
476:
1262:
2045:
1999:
1966:
1662:
1568:
1442:
1397:
1382:
509:
300:
200:
151:
109:
150:
Hydroperoxides are typically more volatile than the corresponding
2007:
1931:
1782:
1777:
1742:
1727:
1722:
1692:
1675:
1499:
1426:
1392:
1030:. PATAI'S Chemistry of Functional Groups. John Wiley & Sons.
358:
2095:
2027:
1871:
1580:
1573:
1467:
1448:
1437:
1421:
1367:
1116:
480:
Synthesis of hydroperoxides of alkene and singlet oxygen in an
455:
447:
443:
376:
241:
113:
430:
1976:
1946:
1879:
1737:
1702:
1697:
1670:
1618:
1585:
1489:
1313:
554:
439:
266:
117:
1081:
1404:
817:
followed by the lyase-induced formation of the hemiacetal.
41:
of the form ROOH, where R stands for any group, typically
1147:, pp. 41–42, Spektrum Akademischer Verlag, Munich, 2004,
1028:
Syntheses and Uses of Hydroperoxides and Dialkylperoxides
793:
361:
are prepared using hydroperoxides as reagents in the
933:
833:
1188:
1080:
868:
2223:
1025:
512:. Important compounds made in this way include
1084:Ullmann's Encyclopedia of Industrial Chemistry
937:Ullmann's Encyclopedia of Industrial Chemistry
837:Ullmann's Encyclopedia of Industrial Chemistry
1278:
1026:Roger A. Sheldon (1983). Patai, Saul (ed.).
377:Production of cyclohexanone and caprolactone
1225:
1115:
968:
277:, as described in this idealized equation:
1285:
1271:
900:
235:
1163:
1161:
625:
350:(TBHP) is employed for the production of
338:
1191:Journal of the American Chemical Society
971:Journal of the American Chemical Society
813:to the hydroperoxide by the action of a
800:
475:
429:
18:
1074:
1021:
1019:
732:Further replacement of alcohol groups:
2224:
1231:
1158:
995:
927:
903:PATAI'S Chemistry of Functional Groups
553:reaction is also observed with common
462:intermediates. Such reactions rely on
1292:
1266:
244:. The range is indicated by 11.5 for
1182:
1016:
53:). Hydroperoxide also refers to the
13:
794:Naturally occurring hydroperoxides
492:
367:
14:
2258:
434:Synthesis of cumene hydroperoxide
425:
73:. Such compounds are a subset of
1234:Current Opinion in Plant Biology
542:
357:Of specialized interest, chiral
131:bond is relatively weak, with a
120:-like). Characteristically, the
100:in peroxides is about 1.45
45:, which contain the hydroperoxy
1209:
1137:
1109:
1221:10.1002/047084289X.rt363m.pub2
1042:
989:
962:
894:
862:
827:
809:is generated by conversion of
1:
821:
573:. An illustrative product is
88:
487:
7:
16:Class of chemical compounds
10:
2263:
522:ethylbenzene hydroperoxide
240:Hydroperoxides are mildly
83:unsaturated chemical bonds
2180:
2139:
2059:
2036:
1998:
1975:
1870:
1791:
1661:
1638:
1594:
1537:
1460:
1435:
1300:
1246:10.1016/j.pbi.2006.03.002
1036:10.1002/9780470771730.ch6
911:10.1002/9780470771730.ch2
905:. Wiley. pp. 85–96.
501:, the direct reaction of
372:The Sharpless epoxidation
275:lithium aluminium hydride
1130:10.15227/orgsyn.034.0090
1093:10.1002/14356007.a08_217
1068:10.15227/orgsyn.063.0066
946:10.1002/14356007.a19_199
846:10.1002/14356007.a19_199
579:butylated hydroxytoluene
514:tert-butyl hydroperoxide
454:or Hock process for its
348:tert-butyl hydroperoxide
133:bond dissociation energy
2191:chemical classification
1087:. Weinheim: Wiley-VCH.
940:. Weinheim: Wiley-VCH.
840:. Weinheim: Wiley-VCH.
333:
315:also effect reduction:
236:Miscellaneous reactions
818:
626:From hydrogen peroxide
575:diethyl ether peroxide
484:
435:
373:
339:Precursors to epoxides
265:Hydroperoxides can be
71:organic hydroperoxides
27:
2198:chemical nomenclature
804:
479:
433:
371:
363:Sharpless epoxidation
22:
998:Analytical Chemistry
518:cumene hydroperoxide
482:Schenck ene reaction
460:cumene hydroperoxide
217:cumene hydroperoxide
127:are about 120°. The
67:hydroperoxyl radical
1654:not C, H or O)
1203:10.1021/ja01638a012
1171:, Wiley-VCH, 2001,
1167:Heinz G. O. Becker
1010:10.1021/ac60121a022
983:10.1021/ja01150a073
882:(50): 12758–12765.
313:tertiary phosphines
55:hydroperoxide anion
2096:Hypervalent iodine
819:
485:
464:radical initiators
436:
374:
116:) are about 110° (
81:in materials with
65:, and the neutral
28:
2247:Functional groups
2237:Organic compounds
2232:Organic peroxides
2219:
2218:
2157:Sulfenyl chloride
2135:
2134:
1634:
1633:
1453:(only C, H and O)
1294:Functional groups
920:978-0-470-77173-0
888:10.1021/ja961838i
876:J. Am. Chem. Soc.
716:C(OH)OOH → [R
563:diisopropyl ether
75:organic peroxides
2254:
2186:
2091:Trifluoromethoxy
1659:
1658:
1655:
1458:
1457:
1454:
1307:
1287:
1280:
1273:
1264:
1263:
1258:
1257:
1229:
1223:
1213:
1207:
1206:
1197:(9): 2322–2325.
1186:
1180:
1165:
1156:
1141:
1135:
1133:
1113:
1107:
1106:
1078:
1072:
1071:
1051:Sharpless, K. B.
1046:
1040:
1039:
1023:
1014:
1013:
993:
987:
986:
966:
960:
959:
931:
925:
924:
898:
892:
891:
866:
860:
859:
831:
789:
778:
728:
699:
653:
621:
546:
534:
507:
472:
415:
329:
309:phosphite esters
295:
261:
252:
230:
222:
212:
207:
198:
193:
182:
171:
146:
142:
138:
130:
123:
107:
96:
60:
52:
47:functional group
2262:
2261:
2257:
2256:
2255:
2253:
2252:
2251:
2222:
2221:
2220:
2215:
2184:
2176:
2131:
2086:Trichloromethyl
2081:Trifluoromethyl
2055:
2032:
1994:
1971:
1866:
1835:Phosphine oxide
1787:
1653:
1651:
1650:
1648:
1646:
1644:
1642:
1640:
1630:
1590:
1533:
1452:
1451:
1446:
1441:
1431:
1305:
1304:
1296:
1291:
1261:
1230:
1226:
1214:
1210:
1187:
1183:
1166:
1159:
1142:
1138:
1114:
1110:
1103:
1079:
1075:
1047:
1043:
1024:
1017:
994:
990:
967:
963:
956:
932:
928:
921:
899:
895:
867:
863:
856:
832:
828:
824:
796:
787:
783:
776:
772:
768:
764:
760:
756:
752:
748:
744:
740:
736:
727:
723:
719:
715:
711:
707:
697:
693:
689:
685:
681:
677:
673:
669:
665:
661:
651:
647:
643:
639:
635:
628:
620:
616:
612:
608:
604:
600:
596:
592:
588:
567:tetrahydrofuran
538:
532:
528:
506:
502:
495:
493:By autoxidation
490:
471:
467:
438:Compounds with
428:
413:
409:
405:
401:
397:
393:
389:
379:
352:propylene oxide
341:
336:
327:
323:
319:
305:sodium ethoxide
293:
289:
285:
281:
259:
255:
250:
246:
238:
228:
220:
210:
205:
201:
196:
191:
187:
180:
169:
144:
140:
136:
128:
125:dihedral angles
121:
105:
94:
91:
58:
50:
17:
12:
11:
5:
2260:
2250:
2249:
2244:
2242:Food additives
2239:
2234:
2217:
2216:
2214:
2213:
2212:
2211:
2206:
2194:
2187:
2181:
2178:
2177:
2175:
2174:
2172:Sulfinylamines
2169:
2164:
2159:
2154:
2152:Phosphoramides
2149:
2147:Isothiocyanate
2143:
2141:
2137:
2136:
2133:
2132:
2130:
2129:
2124:
2123:
2122:
2112:
2111:
2110:
2100:
2099:
2098:
2093:
2088:
2083:
2078:
2067:
2065:
2057:
2056:
2054:
2053:
2048:
2042:
2040:
2034:
2033:
2031:
2030:
2025:
2023:Selenenic acid
2020:
2018:Seleninic acid
2015:
2013:Selenonic acid
2010:
2004:
2002:
1996:
1995:
1993:
1992:
1987:
1981:
1979:
1973:
1972:
1970:
1969:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1893:
1892:
1882:
1876:
1874:
1868:
1867:
1865:
1864:
1859:
1854:
1849:
1848:
1847:
1837:
1832:
1827:
1822:
1821:
1820:
1810:
1809:
1808:
1806:Phosphodiester
1797:
1795:
1789:
1788:
1786:
1785:
1780:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1684:
1683:
1678:
1667:
1665:
1656:
1652:(one element,
1636:
1635:
1632:
1631:
1629:
1628:
1627:
1626:
1616:
1615:
1614:
1609:
1598:
1596:
1592:
1591:
1589:
1588:
1583:
1578:
1577:
1576:
1566:
1565:
1564:
1559:
1554:
1543:
1541:
1535:
1534:
1532:
1531:
1529:Methylenedioxy
1526:
1521:
1520:
1519:
1514:
1504:
1503:
1502:
1497:
1487:
1486:
1485:
1475:
1470:
1464:
1462:
1455:
1433:
1432:
1430:
1429:
1424:
1419:
1418:
1417:
1412:
1402:
1401:
1400:
1395:
1390:
1385:
1380:
1375:
1365:
1364:
1363:
1358:
1348:
1347:
1346:
1341:
1336:
1331:
1326:
1321:
1310:
1308:
1306:(only C and H)
1298:
1297:
1290:
1289:
1282:
1275:
1267:
1260:
1259:
1224:
1208:
1181:
1157:
1136:
1108:
1102:978-3527306732
1101:
1073:
1041:
1015:
988:
961:
955:978-3527306732
954:
926:
919:
893:
861:
855:978-3527306732
854:
825:
823:
820:
811:linolenic acid
795:
792:
785:
780:
779:
774:
770:
766:
762:
758:
754:
750:
746:
742:
738:
730:
729:
725:
721:
717:
713:
709:
701:
700:
695:
691:
687:
683:
679:
675:
671:
667:
663:
655:
654:
649:
645:
641:
637:
627:
624:
623:
622:
618:
614:
610:
606:
602:
598:
594:
590:
551:Auto-oxidation
548:
547:
536:
535:
530:
504:
494:
491:
489:
486:
469:
452:Cumene process
427:
426:Hock processes
424:
417:
416:
411:
407:
403:
399:
395:
391:
378:
375:
345:Halcon process
340:
337:
335:
332:
331:
330:
325:
321:
297:
296:
291:
287:
283:
282:4 ROOH + LiAlH
257:
248:
237:
234:
233:
232:
214:
203:
189:
184:
90:
87:
79:polymerisation
31:Hydroperoxides
15:
9:
6:
4:
3:
2:
2259:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2229:
2227:
2210:
2207:
2205:
2202:
2201:
2200:
2199:
2195:
2193:
2192:
2188:
2183:
2182:
2179:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2148:
2145:
2144:
2142:
2138:
2128:
2125:
2121:
2118:
2117:
2116:
2113:
2109:
2106:
2105:
2104:
2101:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2073:
2072:
2069:
2068:
2066:
2064:
2063:
2058:
2052:
2051:Telluroketone
2049:
2047:
2044:
2043:
2041:
2039:
2035:
2029:
2026:
2024:
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2005:
2003:
2001:
1997:
1991:
1988:
1986:
1983:
1982:
1980:
1978:
1974:
1968:
1965:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1937:Sulfonic acid
1935:
1933:
1930:
1928:
1927:Sulfinic acid
1925:
1923:
1922:Thiosulfonate
1920:
1918:
1915:
1913:
1912:Thiosulfinate
1910:
1908:
1907:Sulfenic acid
1905:
1903:
1900:
1898:
1895:
1891:
1888:
1887:
1886:
1883:
1881:
1878:
1877:
1875:
1873:
1869:
1863:
1862:Phosphaallene
1860:
1858:
1857:Phosphaalkyne
1855:
1853:
1852:Phosphaalkene
1850:
1846:
1843:
1842:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1819:
1816:
1815:
1814:
1811:
1807:
1804:
1803:
1802:
1799:
1798:
1796:
1794:
1790:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1682:
1679:
1677:
1674:
1673:
1672:
1669:
1668:
1666:
1664:
1660:
1657:
1637:
1625:
1622:
1621:
1620:
1617:
1613:
1610:
1608:
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1600:
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1587:
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1579:
1575:
1572:
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1567:
1563:
1560:
1558:
1555:
1553:
1550:
1549:
1548:
1545:
1544:
1542:
1540:
1536:
1530:
1527:
1525:
1524:Ethylenedioxy
1522:
1518:
1515:
1513:
1510:
1509:
1508:
1505:
1501:
1498:
1496:
1493:
1492:
1491:
1488:
1484:
1481:
1480:
1479:
1476:
1474:
1471:
1469:
1466:
1465:
1463:
1459:
1456:
1450:
1444:
1439:
1434:
1428:
1425:
1423:
1420:
1416:
1413:
1411:
1408:
1407:
1406:
1403:
1399:
1396:
1394:
1391:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1370:
1369:
1366:
1362:
1359:
1357:
1354:
1353:
1352:
1349:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1322:
1320:
1317:
1316:
1315:
1312:
1311:
1309:
1303:
1299:
1295:
1288:
1283:
1281:
1276:
1274:
1269:
1268:
1265:
1255:
1251:
1247:
1243:
1240:(3): 274–80.
1239:
1235:
1228:
1222:
1218:
1212:
1204:
1200:
1196:
1192:
1185:
1178:
1177:3-527-29985-8
1174:
1170:
1164:
1162:
1154:
1153:3-8274-1579-9
1150:
1146:
1143:Brückner, R.
1140:
1131:
1127:
1123:
1119:
1112:
1104:
1098:
1094:
1090:
1086:
1085:
1077:
1069:
1065:
1061:
1058:
1057:
1052:
1049:Hill, J. G.;
1045:
1037:
1033:
1029:
1022:
1020:
1011:
1007:
1003:
999:
992:
984:
980:
976:
972:
965:
957:
951:
947:
943:
939:
938:
930:
922:
916:
912:
908:
904:
897:
889:
885:
881:
878:
877:
872:
865:
857:
851:
847:
843:
839:
838:
830:
826:
816:
812:
808:
807:cis-3-hexenal
803:
799:
791:
735:
734:
733:
706:
705:
704:
660:
659:
658:
634:
633:
632:
587:
586:
585:
582:
580:
576:
572:
568:
564:
560:
559:diethyl ether
556:
552:
545:
541:
540:
539:
527:
526:
525:
523:
519:
515:
511:
500:
483:
478:
474:
465:
461:
457:
453:
449:
445:
441:
432:
423:
421:
388:
387:
386:
384:
383:cyclohexanone
370:
366:
364:
360:
355:
353:
349:
346:
318:
317:
316:
314:
310:
306:
302:
280:
279:
278:
276:
272:
268:
263:
253:
243:
226:
225:cumyl alcohol
218:
215:
208:
194:
185:
178:
176:
167:
163:
161:
157:
156:
155:
153:
148:
134:
126:
119:
115:
111:
103:
99:
86:
84:
80:
76:
72:
68:
64:
56:
48:
44:
40:
36:
32:
26:
21:
2196:
2189:
2103:Vinyl halide
2060:
1990:Borinic acid
1985:Boronic acid
1962:Thioxanthate
1511:
1302:Hydrocarbons
1237:
1233:
1227:
1211:
1194:
1190:
1184:
1168:
1144:
1139:
1121:
1117:
1111:
1082:
1076:
1059:
1054:
1044:
1027:
1001:
997:
991:
974:
970:
964:
935:
929:
902:
896:
879:
874:
870:
864:
835:
829:
815:lipoxygenase
797:
781:
731:
702:
656:
629:
583:
549:
537:
499:autoxidation
496:
437:
418:
380:
356:
342:
298:
264:
254:to 13.1 for
239:
174:
159:
149:
108:angles (R =
92:
70:
54:
34:
30:
29:
2167:Thiocyanate
2162:Sulfonamide
2127:Perchlorate
2115:Acyl halide
2076:Fluoroethyl
1957:Thionoester
1845:Phosphonium
1830:Phosphinate
1825:Phosphonous
1813:Phosphonate
1512:Hydroperoxy
1334:Cyclopropyl
1179:pp. 206–207
1155:(in German)
1056:Org. Synth.
977:(6): 2676.
571:1,4-dioxane
420:Drying oils
179:(b.p. 82-83
98:bond length
2226:Categories
2071:Haloalkane
1942:Thioketone
1897:Persulfide
1793:Phosphorus
1758:Isocyanate
1748:Isonitrile
1649:or oxygen
1647:hydrogen,
1643:not being
1624:Orthoester
1517:Dioxiranes
1495:Enol ether
1383:1-Propenyl
1118:Org. Synth
822:References
617:OCH(OOH)CH
557:, such as
104:, and the
89:Properties
61:) and its
2204:inorganic
2038:Tellurium
1952:Thioester
1917:Sulfoxide
1902:Disulfide
1890:Sulfonium
1840:Phosphine
1818:Phosphite
1801:Phosphate
1733:Carbamate
1708:Hydrazone
1641:element,
1639:Only one
1612:Anhydride
1351:Methylene
1169:Organikum
1004:: 79–81.
871:ab Initio
488:Formation
320:ROOH + PR
301:alkoxides
294:O + 4 ROH
227:(b.p. 202
219:(b.p. 153
39:compounds
2185:See also
2120:Chloride
2046:Tellurol
2000:Selenium
1967:Xanthate
1681:Ammonium
1663:Nitrogen
1645:carbon,
1602:Carboxyl
1569:Aldehyde
1557:Acryloyl
1539:carbonyl
1443:hydrogen
1398:Cumulene
1254:16595187
873:Study".
757:→ [R
678:→ [R
652:C(OH)OOH
510:C-H bond
444:benzylic
359:epoxides
303:such as
271:alcohols
209:(b.p. 65
195:(b.p. 46
152:alcohols
35:peroxols
2209:organic
2008:Selenol
1932:Sulfone
1885:Sulfide
1783:NONOate
1778:Nitroso
1768:Nitrite
1763:Nitrate
1753:Cyanate
1743:Nitrile
1728:Amidine
1723:Imidate
1693:Nitrene
1688:Hydrazo
1676:Enamine
1607:Acetoxy
1595:carboxy
1562:Benzoyl
1500:Epoxide
1483:Methoxy
1473:Alcohol
1427:Carbene
1361:Methine
712:C=O + R
640:C=O + H
533:→ R−OOH
529:R−H + O
450:by the
440:allylic
410:C=O + H
286:→ LiAlO
267:reduced
223:°C) vs
199:°C) vs
172:°C) vs
147:bonds.
122:C−O−O−H
43:organic
25:organic
2108:Iodide
2028:Selone
1872:Sulfur
1581:Ketone
1574:Ketene
1552:Acetyl
1507:Peroxy
1478:Alkoxy
1468:Acetal
1449:oxygen
1438:carbon
1422:Alkyne
1415:Benzyl
1410:Phenyl
1393:Allene
1388:Crotyl
1368:Alkene
1356:Bridge
1344:Pentyl
1329:Propyl
1319:Methyl
1252:
1175:
1151:
1124:: 90.
1099:
1062:: 66.
952:
917:
852:
741:C(OH)]
737:[R
720:C(OH)]
662:[R
597:OCH=CH
569:, and
555:ethers
456:cumene
448:phenol
307:. The
242:acidic
229:
221:
211:
197:
181:
170:
162:-BuOOH
143:, and
2140:Other
1977:Boron
1947:Thial
1880:Thiol
1773:Nitro
1738:Imide
1718:Amide
1703:Oxime
1698:Imine
1671:Amine
1619:Ester
1586:Ynone
1490:Ether
1461:R-O-R
1436:Only
1378:Allyl
1373:Vinyl
1339:Butyl
1324:Ethyl
1314:Alkyl
773:+ 2 H
749:+ 2 H
694:+ 2 H
402:→ (CH
328:+ ROH
324:→ OPR
290:+ 2 H
273:with
177:-BuOH
118:water
106:R−O−O
63:salts
2062:Halo
1547:Acyl
1447:and
1405:Aryl
1250:PMID
1173:ISBN
1149:ISBN
1097:ISBN
950:ISBN
915:ISBN
850:ISBN
788:COOH
520:and
458:and
442:and
334:Uses
311:and
260:COOH
175:tert
166:b.p.
160:tert
93:The
51:−OOH
37:are
1713:Azo
1242:doi
1217:doi
1199:doi
1126:doi
1089:doi
1064:doi
1032:doi
1006:doi
979:doi
942:doi
907:doi
884:doi
880:118
842:doi
765:H)]
761:C(O
670:H)]
666:C(O
648:→ R
609:→ C
601:+ H
398:+ O
365:.
269:to
251:OOH
231:°C)
213:°C)
192:OOH
183:°C)
145:C−O
141:C−H
137:C−C
129:O−O
95:O−O
59:OOH
33:or
2228::
1445:,
1440:,
1248:.
1236:.
1195:76
1193:.
1160:^
1122:34
1120:.
1095:.
1060:63
1018:^
1002:29
1000:.
975:73
973:.
948:.
913:.
848:.
790:.
784:Ph
686:(O
682:C]
565:,
561:,
524::
516:,
396:12
385::
354:.
262:.
256:Ph
247:CH
206:OH
202:CH
188:CH
168:36
154::
139:,
112:,
85:.
1286:e
1279:t
1272:v
1256:.
1244::
1238:9
1219::
1205:.
1201::
1134:.
1132:.
1128::
1105:.
1091::
1070:.
1066::
1038:.
1034::
1012:.
1008::
985:.
981::
958:.
944::
923:.
909::
890:.
886::
858:.
844::
786:3
777:O
775:2
771:2
769:O
767:2
763:2
759:2
755:2
753:O
751:2
747:2
745:O
743:2
739:2
726:2
724:O
722:2
718:2
714:2
710:2
708:R
698:O
696:2
692:2
690:)
688:2
684:2
680:2
676:2
674:O
672:2
668:2
664:2
650:2
646:2
644:O
642:2
638:2
636:R
619:3
615:5
613:H
611:2
607:2
605:O
603:2
599:2
595:5
593:H
591:2
589:C
531:2
505:2
503:O
470:2
468:O
414:O
412:2
408:5
406:)
404:2
400:2
394:H
392:6
390:C
326:3
322:3
292:2
288:2
284:4
258:3
249:3
204:3
190:3
164:(
114:C
110:H
102:Å
57:(
49:(
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