232:
527:
565:
498:
27:
548:
anion is stabilized by resonance. This effect becomes more pronounced as more alkenes are involved to create greater stability. For example, deprotonation at position 3 of a 1,4-diene or position 5 of a 1,3-diene give a
773:
Hayashi T, Ueyama K, Tokunaga N, Yoshida K (2003). "A Chiral
Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts: Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition".
1607:
1189:
1128:
1597:
1592:
1113:
600:
are labile. In some cases, dienes are spectator ligands, remaining coordinated throughout a catalytic cycle and influencing the product distributions.
1579:
1100:
1171:
637:
1619:
1140:
596:. In some cases they serve as placeholder ligands, being removed during a catalytic cycle. For example, the cyclooctadiene ("cod") ligands in
1665:
1680:
1675:
1660:
1245:
1749:
1718:
1497:
1487:
1372:
1754:
1733:
1728:
1512:
1507:
1502:
1492:
1387:
1382:
1377:
1367:
1033:
874:
613:
722:"2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram Display of Azide and Cyanide Components on a Versatile Scaffold"
497:
160:. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in
684:
120:
70:
213:
double bonds separated by one single bond. Conjugated dienes are more stable than other dienes because of resonance.
1799:
490:
by both 1,2-addition and 1,4-addition pathways. Addition of polar reagents can generate complex architectures:
609:
359:
of conjugated dienes. For example, 1,5-cyclooctadiene and 4-vinylcyclohexene are produced by dimerization of
597:
605:
867:
593:
463:
340:
192:
Dienes can be divided into three classes, depending on the relative location of the double bonds:
1259:
512:
297:
which replace unsaturated carbon atoms, giving structures that could more specifically be called
157:
2209:
1023:
558:
471:
466:. Many specialized dienes have been developed to exploit this reactivity for the synthesis of
219:
have the double bonds separated by two or more single bonds. They are usually less stable than
553:
anion. An even greater effect is seen if the anion is aromatic, for example, deprotonation of
2270:
2204:
860:
405:
and 1,9-decadiene, useful crosslinking agents and synthetic intermediates, are produced from
1788:
1587:
576:
568:
267:, an unconjugated diene (notice that each double bond is two carbons away from the other).
19:
This article is about organic chemicals. For the surname "Diene" used in West Africa, see
8:
2116:
726:
336:
177:
2303:
2260:
1118:
1108:
810:
750:
721:
406:
264:
199:
have the double bonds sharing a common atom. The result is more specifically called an
2194:
2166:
2009:
1769:
1764:
1602:
1123:
838:
830:
791:
755:
706:
680:
356:
325:
280:
210:
165:
161:
134:
37:
676:
647:
2158:
822:
783:
745:
735:
672:
651:
642:
439:
348:
344:
317:
85:
47:
335:
In the laboratory, more directed and more delicate processes are employed such as
2329:
2308:
2265:
2174:
2048:
1013:
1003:
554:
467:
352:
826:
720:
Díaz, David Díaz; Converso, Antonella; Sharpless, K. Barry; Finn, M. G. (2006).
701:
2239:
2234:
2199:
2150:
2056:
1028:
1018:
447:
435:
2323:
1916:
1723:
1713:
1209:
834:
646:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
402:
360:
272:
256:
30:
655:
2022:
1986:
1882:
1655:
1645:
1554:
1544:
1534:
1075:
1065:
1055:
842:
795:
759:
371:
20:
231:
2070:
2027:
2000:
1934:
1897:
1816:
1670:
1650:
1637:
1569:
1564:
1559:
1549:
1539:
1526:
1357:
1090:
1085:
1080:
1070:
1060:
1047:
883:
550:
526:
451:
410:
398:
251:, also known as 2-methyl-1,3-butadiene, the precursor to natural rubber.
138:
2129:
2017:
1821:
1708:
1698:
1627:
1362:
1184:
1179:
1154:
1008:
998:
375:
367:
294:
787:
2134:
1872:
1841:
1831:
1826:
1703:
1431:
1219:
1214:
993:
740:
719:
601:
289:
181:
434:
The most heavily practiced reaction of alkenes, dienes included, is
2298:
2293:
2103:
2095:
2087:
1967:
1959:
1951:
1902:
1887:
1877:
1867:
1862:
1836:
1759:
1471:
1451:
1301:
1229:
1224:
1204:
564:
516:
487:
443:
329:
248:
2255:
2229:
2079:
1924:
1857:
1456:
1446:
1436:
1326:
1316:
1306:
1194:
1160:
1148:
962:
952:
942:
932:
483:
305:
173:
169:
604:
dienes have also been described. Other diene complexes include
26:
2124:
2043:
1943:
1892:
1466:
1461:
1441:
1401:
1341:
1336:
1331:
1321:
1311:
1272:
1199:
977:
972:
967:
957:
947:
937:
902:
852:
589:
321:
240:
220:
200:
146:
142:
59:
1808:
1774:
666:
545:
304:
Compounds that contain more than two double bonds are called
772:
541:
103:
97:
91:
56:
351:. Families of nonconjugated dienes are derived from the
109:
667:
Lionel
Delaude; Alfred F. Noels (2005). "Metathesis".
121:
112:
106:
71:
62:
100:
88:
53:
462:An important reaction for conjugated dienes is the
94:
50:
316:On an industrial scale, butadiene is prepared by
2321:
413:, respectively. The catalyst is derived from Re
293:definition, a "diene" could include one or more
275:, a strained bicyclic and unconjugated diene.
223:conjugated dienes. This can also be known as an
16:Covalent compound that contains two double bonds
901:
669:Kirk-Othmer Encyclopedia of Chemical Technology
811:"Chiral Diene Ligands in Asymmetric Catalysis"
702:"9-Thiabicyclo[3.3.1]nonane-2,6-dione"
633:
631:
629:
868:
308:. Polyenes and dienes share many properties.
809:Huang, Yinhua; Hayashi, Tamio (2022-09-28).
808:
515:reactions. These reactions require a metal
626:
477:
875:
861:
540:The position adjacent to a double bond is
454:is related but it is a synthetic monomer.
749:
739:
699:
563:
511:Nonconjugated dienes are substrates for
324:. In a similarly non-selective process,
230:
25:
506:
482:Conjugated dienes add reagents such as
259:, a precursor to synthetic polymers.
2322:
424:
311:
856:
614:cyclooctadiene rhodium chloride dimer
397:. They are prepared industrially by
438:. 1,3-Butadiene is a precursor to
243:, is the simplest cumulated diene.
13:
643:Compendium of Chemical Terminology
14:
2341:
660:
588:Dienes are widely used chelating
457:
429:
347:have been developed, such as the
882:
525:
496:
401:of cyclic dienes. For example,
239:: 1,2-Propadiene, also known as
152:units, with the standard prefix
84:
46:
677:10.1002/0471238961.metanoel.a01
381:α,ω-Dienes have the formula (CH
802:
766:
693:
610:cyclobutadieneiron tricarbonyl
1:
619:
583:
145:atoms. They thus contain two
598:bis(cyclooctadiene)nickel(0)
7:
827:10.1021/acs.chemrev.2c00218
606:(butadiene)iron tricarbonyl
10:
2346:
716:, vol. 9, p. 692
535:
187:
168:dienes are widely used as
18:
2286:
2248:
2222:
2187:
2143:
2115:
2078:
2069:
2036:
2008:
1999:
1979:
1942:
1933:
1915:
1850:
1807:
1798:
1787:
1742:
1689:
1636:
1618:
1578:
1525:
1480:
1424:
1400:
1350:
1294:
1271:
1258:
1238:
1170:
1139:
1099:
1046:
986:
925:
890:
594:organometallic chemistry
478:Other addition reactions
671:. Weinheim: Wiley-VCH.
656:10.1351/goldbook.D01699
513:ring-closing metathesis
158:systematic nomenclature
2210:1,3,5-Triheptylbenzene
580:
559:cyclopentadienyl anion
544:because the resulting
284:
33:
2205:1,3,5-Triethylbenzene
575:diene ligand used in
567:
234:
29:
1608:Isopropylcyclohexene
1190:Perhydrophenanthrene
1129:Isopropylcyclohexane
577:asymmetric catalysis
507:Metathesis reactions
464:Diels–Alder reaction
446:is the precursor to
337:dehydrohalogenations
178:Polyunsaturated fats
2304:Alicyclic compounds
2117:Tetramethylbenzenes
821:(18): 14346–14404.
782:(38): 11508–11509.
472:Danishefsky's diene
442:used in tires, and
425:Reactivity and uses
312:Synthesis of dienes
217:Unconjugated dienes
180:are of interest to
2261:Cyclopropenylidene
1598:Methylcyclopentene
1588:Methylcyclopropene
1119:Methylcyclopentane
1109:Methylcyclopropane
581:
407:1,5-cyclooctadiene
285:
265:1,5-Cyclooctadiene
137:that contains two
34:
2317:
2316:
2282:
2281:
2218:
2217:
2195:Hexamethylbenzene
2183:
2182:
2065:
2064:
2010:Trimethylbenzenes
1995:
1994:
1911:
1910:
1783:
1782:
1770:Cyclododecatriene
1765:Cyclooctatetraene
1603:Methylcyclohexene
1593:Methylcyclobutene
1580:Alkylcycloalkenes
1521:
1520:
1396:
1395:
1254:
1253:
1124:Methylcyclohexane
1114:Methylcyclobutane
1101:Alkylcycloalkanes
1042:
1041:
788:10.1021/ja037367z
714:Collected Volumes
707:Organic Syntheses
366:Diene-containing
328:is obtained from
326:dicyclopentadiene
287:According to the
281:Dicyclopentadiene
207:Conjugated dienes
162:organic synthesis
135:covalent compound
38:organic chemistry
2337:
2274:-Propenylbenzene
2076:
2075:
2006:
2005:
1940:
1939:
1931:
1930:
1805:
1804:
1796:
1795:
1481:Branched alkynes
1422:
1421:
1351:Branched alkenes
1292:
1291:
1269:
1268:
1172:Polycycloalkanes
1157:(bicycloheptane)
1151:(bicyclopentane)
987:Branched alkanes
923:
922:
899:
898:
877:
870:
863:
854:
853:
847:
846:
815:Chemical Reviews
806:
800:
799:
776:J. Am. Chem. Soc
770:
764:
763:
753:
743:
741:10.3390/11040212
717:
710:
697:
691:
690:
664:
658:
635:
529:
500:
468:natural products
349:Whiting reaction
318:thermal cracking
197:Cumulated dienes
141:, usually among
125:
119:
118:
115:
114:
111:
108:
105:
102:
99:
96:
93:
90:
74:
69:
68:
65:
64:
61:
58:
55:
52:
2345:
2344:
2340:
2339:
2338:
2336:
2335:
2334:
2320:
2319:
2318:
2313:
2309:Petroleum jelly
2278:
2266:Phenylacetylene
2244:
2214:
2179:
2175:Isobutylbenzene
2139:
2111:
2061:
2032:
1991:
1975:
1929:
1907:
1846:
1790:
1779:
1738:
1685:
1632:
1614:
1574:
1517:
1476:
1418:
1410:
1404:
1392:
1346:
1288:
1281:
1275:
1264:
1262:
1250:
1234:
1166:
1163:(bicyclodecane)
1135:
1095:
1038:
1004:3-Methylpentane
982:
919:
911:
905:
894:
892:
886:
881:
851:
850:
807:
803:
771:
767:
712:
698:
694:
687:
665:
661:
636:
627:
622:
586:
572:
555:cyclopentadiene
538:
509:
480:
460:
432:
427:
420:
416:
396:
392:
388:
384:
353:oligomerization
314:
190:
123:
87:
83:
72:
49:
45:
24:
17:
12:
11:
5:
2343:
2333:
2332:
2315:
2314:
2312:
2311:
2306:
2301:
2296:
2290:
2288:
2284:
2283:
2280:
2279:
2277:
2276:
2268:
2263:
2258:
2252:
2250:
2246:
2245:
2243:
2242:
2240:4-Vinyltoluene
2237:
2235:Divinylbenzene
2232:
2226:
2224:
2220:
2219:
2216:
2215:
2213:
2212:
2207:
2202:
2200:2-Phenylhexane
2197:
2191:
2189:
2185:
2184:
2181:
2180:
2178:
2177:
2172:
2164:
2156:
2147:
2145:
2141:
2140:
2138:
2137:
2132:
2127:
2121:
2119:
2113:
2112:
2110:
2109:
2101:
2093:
2084:
2082:
2073:
2067:
2066:
2063:
2062:
2060:
2059:
2057:4-Ethyltoluene
2054:
2052:-Propylbenzene
2046:
2040:
2038:
2034:
2033:
2031:
2030:
2025:
2020:
2014:
2012:
2003:
1997:
1996:
1993:
1992:
1990:
1989:
1983:
1981:
1977:
1976:
1974:
1973:
1965:
1957:
1948:
1946:
1937:
1928:
1927:
1921:
1919:
1913:
1912:
1909:
1908:
1906:
1905:
1900:
1895:
1890:
1885:
1880:
1875:
1870:
1865:
1860:
1854:
1852:
1848:
1847:
1845:
1844:
1839:
1834:
1829:
1824:
1819:
1813:
1811:
1802:
1793:
1785:
1784:
1781:
1780:
1778:
1777:
1772:
1767:
1762:
1757:
1752:
1746:
1744:
1740:
1739:
1737:
1736:
1731:
1726:
1721:
1716:
1711:
1706:
1701:
1695:
1693:
1687:
1686:
1684:
1683:
1678:
1673:
1668:
1663:
1658:
1653:
1648:
1642:
1640:
1634:
1633:
1631:
1630:
1624:
1622:
1620:Bicycloalkenes
1616:
1615:
1613:
1612:
1610:
1605:
1600:
1595:
1590:
1584:
1582:
1576:
1575:
1573:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1531:
1529:
1523:
1522:
1519:
1518:
1516:
1515:
1510:
1505:
1500:
1495:
1490:
1484:
1482:
1478:
1477:
1475:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1428:
1426:
1425:Linear alkynes
1419:
1412:
1406:
1398:
1397:
1394:
1393:
1391:
1390:
1385:
1380:
1375:
1370:
1365:
1360:
1354:
1352:
1348:
1347:
1345:
1344:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1304:
1298:
1296:
1295:Linear alkenes
1289:
1283:
1277:
1266:
1256:
1255:
1252:
1251:
1249:
1248:
1242:
1240:
1236:
1235:
1233:
1232:
1227:
1222:
1217:
1212:
1207:
1202:
1197:
1192:
1187:
1182:
1176:
1174:
1168:
1167:
1165:
1164:
1158:
1152:
1145:
1143:
1141:Bicycloalkanes
1137:
1136:
1134:
1133:
1131:
1126:
1121:
1116:
1111:
1105:
1103:
1097:
1096:
1094:
1093:
1088:
1083:
1078:
1073:
1068:
1063:
1058:
1052:
1050:
1044:
1043:
1040:
1039:
1037:
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
990:
988:
984:
983:
981:
980:
975:
970:
965:
960:
955:
950:
945:
940:
935:
929:
927:
926:Linear alkanes
920:
913:
907:
896:
888:
887:
880:
879:
872:
865:
857:
849:
848:
801:
765:
734:(4): 212–218.
700:Roger Bishop.
692:
685:
659:
624:
623:
621:
618:
585:
582:
570:
537:
534:
533:
532:
531:
530:
508:
505:
504:
503:
502:
501:
479:
476:
459:
458:Cycloadditions
456:
448:natural rubber
436:polymerization
431:
430:Polymerization
428:
426:
423:
418:
414:
394:
390:
386:
382:
372:biosynthesized
313:
310:
229:
228:
214:
204:
189:
186:
15:
9:
6:
4:
3:
2:
2342:
2331:
2328:
2327:
2325:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2292:
2291:
2289:
2285:
2275:
2273:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2253:
2251:
2247:
2241:
2238:
2236:
2233:
2231:
2228:
2227:
2225:
2223:Vinylbenzenes
2221:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2192:
2190:
2186:
2176:
2173:
2171:
2170:-Butylbenzene
2169:
2165:
2163:
2162:-Butylbenzene
2161:
2157:
2155:
2154:-Butylbenzene
2153:
2149:
2148:
2146:
2142:
2136:
2133:
2131:
2128:
2126:
2123:
2122:
2120:
2118:
2114:
2108:
2106:
2102:
2100:
2098:
2094:
2092:
2090:
2086:
2085:
2083:
2081:
2077:
2074:
2072:
2068:
2058:
2055:
2053:
2051:
2047:
2045:
2042:
2041:
2039:
2035:
2029:
2026:
2024:
2021:
2019:
2016:
2015:
2013:
2011:
2007:
2004:
2002:
1998:
1988:
1985:
1984:
1982:
1978:
1972:
1970:
1966:
1964:
1962:
1958:
1956:
1954:
1950:
1949:
1947:
1945:
1941:
1938:
1936:
1932:
1926:
1923:
1922:
1920:
1918:
1917:Alkylbenzenes
1914:
1904:
1901:
1899:
1896:
1894:
1891:
1889:
1886:
1884:
1881:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1856:
1855:
1853:
1849:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1814:
1812:
1810:
1806:
1803:
1801:
1797:
1794:
1792:
1786:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1747:
1745:
1741:
1735:
1732:
1730:
1727:
1725:
1722:
1720:
1717:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1697:
1696:
1694:
1692:
1688:
1682:
1679:
1677:
1674:
1672:
1669:
1667:
1664:
1662:
1659:
1657:
1654:
1652:
1649:
1647:
1644:
1643:
1641:
1639:
1635:
1629:
1626:
1625:
1623:
1621:
1617:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1591:
1589:
1586:
1585:
1583:
1581:
1577:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1541:
1538:
1536:
1533:
1532:
1530:
1528:
1524:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1485:
1483:
1479:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1429:
1427:
1423:
1420:
1416:
1409:
1403:
1399:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1369:
1366:
1364:
1361:
1359:
1356:
1355:
1353:
1349:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1303:
1300:
1299:
1297:
1293:
1290:
1287:
1280:
1274:
1270:
1267:
1261:
1257:
1247:
1244:
1243:
1241:
1237:
1231:
1228:
1226:
1223:
1221:
1218:
1216:
1213:
1211:
1210:Dodecahedrane
1208:
1206:
1203:
1201:
1198:
1196:
1193:
1191:
1188:
1186:
1183:
1181:
1178:
1177:
1175:
1173:
1169:
1162:
1159:
1156:
1153:
1150:
1147:
1146:
1144:
1142:
1138:
1132:
1130:
1127:
1125:
1122:
1120:
1117:
1115:
1112:
1110:
1107:
1106:
1104:
1102:
1098:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1053:
1051:
1049:
1045:
1035:
1032:
1030:
1027:
1025:
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
995:
992:
991:
989:
985:
979:
976:
974:
971:
969:
966:
964:
961:
959:
956:
954:
951:
949:
946:
944:
941:
939:
936:
934:
931:
930:
928:
924:
921:
917:
910:
904:
900:
897:
889:
885:
878:
873:
871:
866:
864:
859:
858:
855:
844:
840:
836:
832:
828:
824:
820:
816:
812:
805:
797:
793:
789:
785:
781:
777:
769:
761:
757:
752:
747:
742:
737:
733:
729:
728:
723:
715:
709:
708:
703:
696:
688:
686:0-471-23896-1
682:
678:
674:
670:
663:
657:
653:
649:
645:
644:
639:
634:
632:
630:
625:
617:
615:
611:
607:
603:
599:
595:
591:
578:
574:
566:
562:
560:
556:
552:
547:
543:
528:
524:
523:
522:
521:
520:
518:
514:
499:
495:
494:
493:
492:
491:
489:
485:
475:
473:
469:
465:
455:
453:
449:
445:
441:
437:
422:
412:
408:
404:
403:1,5-hexadiene
400:
379:
377:
373:
369:
364:
362:
361:1,3-butadiene
358:
354:
350:
346:
342:
341:condensations
338:
333:
331:
327:
323:
319:
309:
307:
302:
300:
296:
292:
291:
282:
278:
274:
273:Norbornadiene
270:
266:
262:
258:
257:1,3-Butadiene
254:
250:
246:
242:
238:
235:Some dienes:
233:
226:
222:
218:
215:
212:
208:
205:
202:
198:
195:
194:
193:
185:
183:
179:
175:
171:
167:
163:
159:
155:
151:
150:
144:
140:
136:
132:
128:
127:
117:
81:
77:
76:
67:
43:
39:
32:
31:1,3-butadiene
28:
22:
2271:
2167:
2159:
2151:
2104:
2096:
2088:
2049:
2023:Pseudocumene
1987:Ethylbenzene
1968:
1960:
1952:
1883:Phenanthrene
1791:hydrocarbons
1690:
1666:Cycloheptyne
1656:Cyclopentyne
1646:Cyclopropyne
1638:Cycloalkynes
1555:Cycloheptene
1545:Cyclopentene
1535:Cyclopropene
1527:Cycloalkenes
1414:
1407:
1285:
1278:
1265:hydrocarbons
1246:Spiroalkanes
1076:Cycloheptane
1066:Cyclopentane
1056:Cyclopropane
1048:Cycloalkanes
915:
908:
895:hydrocarbons
884:Hydrocarbons
818:
814:
804:
779:
775:
768:
731:
725:
713:
705:
695:
668:
662:
641:
587:
557:to give the
539:
510:
481:
461:
433:
421:on alumina.
380:
365:
357:dimerization
334:
315:
303:
299:heterodienes
298:
288:
286:
276:
268:
260:
252:
244:
236:
224:
216:
206:
196:
191:
153:
148:
139:double bonds
130:
79:
41:
35:
21:Serer people
2071:C4-Benzenes
2028:Hemellitene
2001:C3-Benzenes
1935:C2-Benzenes
1898:Corannulene
1817:Naphthalene
1681:Cyclodecyne
1676:Cyclononyne
1671:Cyclooctyne
1661:Cyclohexyne
1651:Cyclobutyne
1570:Cyclodecene
1565:Cyclononene
1560:Cyclooctene
1550:Cyclohexene
1540:Cyclobutene
1260:Unsaturated
1091:Cyclodecane
1086:Cyclononane
1081:Cyclooctane
1071:Cyclohexane
1061:Cyclobutane
551:pentadienyl
452:Chloroprene
411:cyclooctene
399:ethenolysis
368:fatty acids
295:heteroatoms
2130:Prehnitene
2018:Mesitylene
1873:Circulenes
1822:Anthracene
1750:Alkatriene
1719:Heptadiene
1709:Pentadiene
1699:Propadiene
1628:Norbornene
1498:Isoheptyne
1488:Isopentyne
1373:Isoheptene
1363:Isopentene
1185:Diamondoid
1180:Adamantane
1155:Norbornane
1019:Isoheptane
1009:Neopentane
999:Isopentane
620:References
584:As ligands
573:-symmetric
376:acetyl CoA
343:. Myriad
211:conjugated
176:industry.
166:Conjugated
2299:Annulynes
2294:Annulenes
2135:Isodurene
1868:Helicenes
1842:Heptacene
1832:Pentacene
1827:Tetracene
1755:Alkadiyne
1734:Decadiene
1729:Nonadiene
1724:Octadiene
1714:Hexadiene
1704:Butadiene
1513:Isodecyne
1508:Isononyne
1503:Isooctyne
1493:Isohexyne
1388:Isodecene
1383:Isononene
1378:Isooctene
1368:Isohexene
1358:Isobutene
1263:aliphatic
1220:Churchane
1215:Basketane
1034:Isodecane
1029:Isononane
1024:Isooctane
1014:Isohexane
994:Isobutane
893:aliphatic
891:Saturated
835:0009-2665
727:Molecules
330:coal tars
290:Gold Book
182:nutrition
131:alkadiene
2324:Category
1903:Kekulene
1888:Chrysene
1878:Butalene
1863:Fluorene
1837:Hexacene
1789:Aromatic
1760:Cumulene
1230:Twistane
1225:Pagodane
1205:Prismane
843:35972018
796:13129348
760:17962753
517:catalyst
488:hydrogen
444:isoprene
306:polyenes
249:Isoprene
225:isolated
221:isomeric
170:monomers
80:diolefin
78:); also
2256:Benzene
2230:Styrene
2107:-Cymene
2099:-Cymene
2091:-Cymene
2080:Cymenes
1971:-Xylene
1963:-Xylene
1955:-Xylene
1944:Xylenes
1925:Toluene
1858:Azulene
1457:Heptyne
1447:Pentyne
1437:Propyne
1402:Alkynes
1327:Heptene
1317:Pentene
1307:Propene
1273:Alkenes
1195:Sterane
1161:Decalin
1149:Housane
963:Heptane
953:Pentane
943:Propane
933:Methane
903:Alkanes
751:6148556
590:ligands
536:Acidity
484:bromine
470:(e.g.,
345:methods
322:butanes
188:Classes
174:polymer
172:in the
133:) is a
126:-lə-fin
2330:Dienes
2125:Durene
2044:Cumene
1893:Pyrene
1809:Acenes
1691:Dienes
1472:Decyne
1467:Nonyne
1462:Octyne
1452:Hexyne
1442:Butyne
1432:Ethyne
1342:Decene
1337:Nonene
1332:Octene
1322:Hexene
1312:Butene
1302:Ethene
1200:Cubane
978:Decane
973:Nonane
968:Octane
958:Hexane
948:Butane
938:Ethane
841:
833:
794:
758:
748:
683:
648:dienes
612:, and
602:Chiral
542:acidic
440:rubber
389:(CH=CH
241:allene
227:diene.
201:allene
143:carbon
2287:Other
2272:trans
2249:Other
2188:Other
2144:Other
2037:Other
1980:Other
1851:Other
1775:Enyne
1743:Other
1239:Other
638:IUPAC
546:allyl
374:from
209:have
129:) or
42:diene
2168:tert
1800:PAHs
839:PMID
831:ISSN
792:PMID
756:PMID
681:ISBN
486:and
409:and
370:are
355:and
339:and
75:-een
40:, a
2160:sec
1417:− 2
918:+ 2
823:doi
819:122
784:doi
780:125
746:PMC
736:doi
673:doi
652:doi
650:".
592:in
519::c
474:).
450:.
320:of
164:.
156:of
149:ene
147:alk
122:dy-
36:In
2326::
837:.
829:.
817:.
813:.
790:.
778:.
754:.
744:.
732:11
730:.
724:.
711:;
704:.
679:.
640:,
628:^
616:.
608:,
561:.
378:.
363:.
332:.
301:.
279::
271::
263::
255::
247::
184:.
154:di
124:OH
98:oʊ
92:aɪ
82:,
73:DY
60:iː
57:aɪ
2152:n
2105:p
2097:m
2089:o
2050:n
1969:p
1961:m
1953:o
1415:n
1413:2
1411:H
1408:n
1405:C
1286:n
1284:2
1282:H
1279:n
1276:C
916:n
914:2
912:H
909:n
906:C
876:e
869:t
862:v
845:.
825::
798:.
786::
762:.
738::
718:.
689:.
675::
654::
579:.
571:2
569:C
419:7
417:O
415:2
395:2
393:)
391:2
387:n
385:)
383:2
283:.
277:F
269:E
261:D
253:C
245:B
237:A
203:.
116:/
113:n
110:ɪ
107:f
104:ə
101:l
95:ˈ
89:d
86:/
66:/
63:n
54:d
51:ˈ
48:/
44:(
23:.
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