334:
893:
929:
401:
149:
439:
465:
31:
707:
837:
1324:
Yus, Miguel; González-Gómez, José C.; Foubelo, Francisco (2013). "Diastereoselective
Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products".
247:
of C−H bonds on a doubly allylic centre is about 10% less than the bond dissociation energy of a C−H bond that is singly allylic. The weakened C−H bonds is reflected in the easy
318:. Metals accelerate the degradation. These fats tend to polymerize, forming semisolids. This reactivity pattern is fundamental to the film-forming behavior of the "
1661:
2580:
882:
858:
Allylation is the attachment of an allyl group to a substrate, usually another organic compound. Classically, allylation involves the reaction of a
1453:
Sakurai Hideki; Hosomi Akira; Hayashi
Josabro (1984). "Conjugate Allylation of α,β-Unsaturated Ketones with Allylsilanes: 4-Phenyl-6-Hepten-2-one".
518:
crosslink via oxygenation of allylic (or doubly allylic) sites. This crosslinking underpins the properties of paints and the spoilage of foods by
2585:
543:
1589:
1188:
429:. All feature three contiguous sp²-hybridized carbon centers and all derive stability from resonance. Each species can be presented by two
202:
and allylic are related in terms of structure, bond strength, and reactivity. Other reactions that tend to occur with allylic compounds are
1418:
Yus, Miguel; González-Gómez, José C.; Foubelo, Francisco (2011). "Catalytic
Enantioselective Allylation of Carbonyl Compounds and Imines".
310:
One practical consequence of their high reactivity is that polyunsaturated fatty acids have poor shelf life owing to their tendency toward
1115:
730:
974:
From the industrial perspective, oxidation of benzylic C-H bonds are conducted on a particularly large scale, e.g. production of
1281:
Nogi, Keisuke; Yorimitsu, Hideki (2021). "Carbon–Carbon Bond
Cleavage at Allylic Positions: Retro-allylation and Deallylation".
1654:
994:
Many substituents can be attached to the allyl group to give stable compounds. Commercially important allyl compounds include:
459:
has three molecular orbitals: the first one bonding, the second one non-bonding, and the higher energy orbital is antibonding.
1257:
1026:
892:
2484:
1252:. The Chemistry of Functional Groups. Vol. 2. London: Interscience / William Clowes & Sons. pp. 56–57.
1030:
333:
1012:
2057:
1647:
264:
1248:
Richey, Herman G. (1970). "The properties of alkene carbonium ions and carbanions". In
Zabicky, Jacob (ed.).
1515:
Horn, Evan J.; Rosen, Brandon R.; Chen, Yong; Tang, Jiaze; Chen, Ke; Eastgate, Martin D.; Baran, Phil S. (2016).
1057:
211:
189:
2613:
2094:
296:
244:
2608:
2567:
1605:
Recupero, Francesco; Punta, Carlo (2007). "Free
Radical Functionalization of Organic Compounds Catalyzed by
2467:
2574:
2462:
1087:
1047:
442:
426:
193:
137:
1572:
Hoekstra, William J.; Fairlamb, Ian J. S.; Giroux, Simon; Chen, Yuzhong (2017). "Selenium(IV) Oxide".
2543:
1988:
1528:
983:
867:
492:
486:
430:
1849:
863:
153:
1497:
1306:
878:
871:
381:
refers to the position on a carbon skeleton next to an allylic position. In but-3-enyl chloride
284:
51:
2533:
2503:
2261:
1883:
1626:
1585:
1554:
1435:
1400:
1351:
1298:
1263:
1253:
1221:
1184:
1111:
975:
227:
203:
133:
39:
1217:
2238:
1732:
1670:
1618:
1577:
1544:
1536:
1489:
1462:
1427:
1390:
1382:
1341:
1333:
1290:
1213:
1159:
937:
886:
276:
98:
65:
2457:
2216:
2211:
2194:
2177:
1978:
1727:
1052:
922:
847:
519:
315:
1532:
2528:
2523:
2399:
2394:
2389:
2182:
2149:
1933:
1915:
1905:
1549:
1516:
1395:
1370:
1110:
Jerry March, "Advanced
Organic Chemistry" 4th Ed. J. Wiley and Sons, 1992: New York.
1042:
1020:
998:
713:
272:
185:
123:
1480:
Maison, Wolfgang; Weidmann, Verena (2013). "Allylic
Oxidations of Olefins to Enones".
928:
303:. Some of these derivatives are signallng molecules, some are used in plant defense (
2602:
2548:
2496:
2427:
2313:
2303:
2298:
2288:
2283:
2233:
2228:
2144:
2139:
2129:
1983:
1938:
1900:
1888:
1859:
1737:
1501:
1310:
843:
526:
353:
300:
288:
268:
2479:
2366:
2361:
2338:
2089:
1928:
1854:
1791:
1786:
1764:
1720:
1705:
1695:
979:
717:
530:
414:
338:
311:
207:
1581:
491:
This heightened reactivity of allylic groups has many practical consequences. The
445:
of the allyl anion. The cation is identical, but carries an opposite-sign charge.
148:
1371:"Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions"
1369:
Weaver, Jimmie D.; Recio, Antonio; Grenning, Alexander J.; Tunge, Jon A. (2011).
1178:
2538:
2491:
2452:
2333:
2221:
2206:
2201:
2189:
1749:
1715:
1710:
1700:
1678:
1294:
1062:
515:
422:
400:
342:
304:
77:
47:
905:
Allylic C-H bonds are susceptible to oxidation. One commercial application of
2447:
2438:
2318:
2273:
2169:
2134:
2124:
2064:
2000:
1923:
1871:
1077:
914:
910:
511:
472:
orbital is singly occupied; in the cation, unoccupied; and in the anion, full.
456:
363:
319:
252:
102:
1466:
1163:
932:
The conversion of valencene to nootkatone is an example of allylic oxidation.
2414:
2328:
2293:
2278:
2266:
2109:
2084:
1893:
918:
859:
721:
702:{\displaystyle {\ce {2CH3-CH=CH2 + 2 NH3 + 3 O2 -> 2CH2=CH-C#N + 6 H2O}}}
468:
MO diagram for allyl π orbitals. In the radical (shown), the intermediate Ψ
452:
418:
397:, the chloride is homoallylic because it is bonded to the homoallylic site.
323:
292:
248:
1630:
1558:
1493:
1439:
1404:
1355:
1302:
1225:
2422:
2376:
2343:
2039:
1945:
1819:
1774:
1759:
1082:
1067:
199:
122:, some of which are of practical or of everyday importance, for example,
1540:
438:
433:
with the charge or unpaired electron distributed at both 1,3 positions.
404:
The allylic, homoallylic and doubly allylic sites are highlighted in red
307:), some are precursors to other metabolites that are used by the plant.
2384:
2308:
2159:
2154:
2119:
2104:
2099:
2069:
2052:
1876:
1803:
1769:
1346:
1072:
1016:
534:
327:
17:
1622:
1431:
1386:
1337:
891:
2472:
2404:
2248:
1957:
1950:
1844:
1825:
1814:
1798:
1744:
1204:
Feussner, Ivo; Wasternack, Claus (2002). "The
Lipoxygenase Pathway".
215:
88:
1639:
1147:
413:
The allyl group is widely encountered in organic chemistry. Allylic
156:
pathway for the first phase of the oxidative rancidification of fats
464:
218:
groups are related to allyl groups; both show enhanced reactivity.
2353:
2323:
2256:
2114:
2079:
2074:
2047:
1995:
1962:
1866:
1690:
964:
927:
463:
437:
399:
332:
147:
29:
1781:
1517:"Scalable and sustainable electrochemical allylic C–H oxidation"
1267:
968:
30:
1643:
832:{\displaystyle {\ce {CH3CH=CH2 + Cl2 -> ClCH2CH=CH2 + HCl}}}
279:. They are susceptible to a range of reactions with oxygen (O
160:
A site adjacent to the unsaturated carbon atom is called the
881:: the addition of an allyl group to the beta-position of an
168:. A group attached at this site is sometimes described as
819:
798:
782:
766:
745:
692:
648:
628:
608:
588:
562:
1131:
Morrison, Robert
Thornton; Boyd, Robert Neilson (1987).
537:
exploits the easy oxidation of the allylic C−H centers:
111:". The term allyl applies to many compounds related to
495:
or various rubbers exploits the conversion of allylic
733:
546:
192:
are about 15% weaker than the C−H bonds in ordinary
87:). The name is derived from the scientific name for
2516:
2436:
2413:
2375:
2352:
2247:
2168:
2038:
2015:
1971:
1914:
1837:
1812:
1677:
1180:Garlic and Other Alliums: The Lore and the Science
1019:, a precursor to many natural products, including
831:
701:
239:group connected to two vinyl groups is said to be
940:is used to convert alkenes to allylic alcohols:
1574:Encyclopedia of Reagents for Organic Synthesis
1655:
889:is a common method for conjugate allylation.
291:, epoxy-hydroxy polyunsaturated fatty acids,
8:
106:
1238:Organic Chemistry John McMurry 2nd ed. 1988
862:with allyl chloride. Alternatives include
196:carbon centers and are thus more reactive.
92:
2035:
1834:
1662:
1648:
1640:
1548:
1394:
1345:
936:In the synthesis of some fine chemicals,
818:
813:
804:
797:
792:
781:
776:
765:
760:
751:
744:
739:
734:
732:
691:
686:
681:
667:
659:
651:
647:
642:
637:
627:
622:
617:
607:
602:
597:
587:
582:
573:
565:
561:
556:
551:
547:
545:
345:features groups with both doubly allylic
1218:10.1146/annurev.arplant.53.100301.135248
505:
498:
392:
388:
384:
348:
258:
235:
179:
175:
118:
114:
83:
71:
60:
56:
1106:
1104:
1102:
1098:
1126:
1124:
712:An estimated 800,000 tonnes (1997) of
314:, leading, in the case of edibles, to
866:with allylmetallic reagents, such as
7:
877:Allylation can be effected also by
101:isolated an allyl derivative from
25:
1015:, central in the biosynthesis of
1152:Annalen der Chemie und Pharmacie
1135:(4th ed.). Allyn and Bacon.
1027:Transition-metal allyl complexes
1148:"Untersuchung des Knoblauchöls"
267:feature this pentadiene group:
1206:Annual Review of Plant Biology
1183:. Royal Society of Chemistry.
921:, a more abundantly available
785:
631:
287:. Products include fatty acid
136:that adds an allyl group to a
1:
1582:10.1002/047084289X.rs008.pub3
1031:allylpalladium chloride dimer
525:The industrial production of
362:) and a singly allylic site (
251:of compounds containing 1,4-
34:Structure of the allyl group
27:Chemical group (–CH₂–CH=CH₂)
1295:10.1021/acs.chemrev.0c00157
1063:Propargylic/Homopropargylic
1013:Dimethylallyl pyrophosphate
870:, or the iridium-catalyzed
322:", which are components of
265:polyunsaturated fatty acids
2630:
484:
481:Reactions and applications
427:intermediates in reactions
225:
2557:
1146:Theodor Wertheim (1844).
1053:Allylic palladium complex
1467:10.15227/orgsyn.062.0086
1250:The Chemistry of Alkenes
1164:10.1002/jlac.18440510302
297:divinylether fatty acids
245:bond dissociation energy
2568:chemical classification
963:where R, R', R" may be
887:Hosomi-Sakurai reaction
842:It is the precursor to
510:crosslinks. Similarly
425:are often discussed as
1494:10.1055/s-0033-1338491
933:
897:
833:
703:
473:
446:
405:
369:
157:
107:
93:
35:
2575:chemical nomenclature
1609:Hydroxyphthalimide".
1088:Allylic rearrangement
1048:Carroll rearrangement
931:
896:insert a caption here
895:
834:
704:
467:
441:
403:
336:
151:
33:
1058:Tsuji–Trost reaction
984:cumene hydroperoxide
909:is the synthesis of
868:allyltrimethylsilane
731:
544:
493:sulfur vulcanization
487:Allylic substitution
431:resonance structures
360:alpha-linolenic acid
212:Tsuji–Trost reaction
2031:not C, H or O)
1541:10.1038/nature17431
1533:2016Natur.533...77H
1177:Eric Block (2010).
913:, the fragrance of
864:carbonyl allylation
821:
800:
784:
768:
747:
716:is produced by the
694:
650:
630:
610:
590:
564:
443:Resonance structure
64:. It consists of a
2473:Hypervalent iodine
934:
898:
879:conjugate addition
872:Krische allylation
829:
809:
788:
772:
756:
735:
699:
682:
638:
618:
598:
578:
552:
474:
447:
406:
370:
285:lipid peroxidation
283:), starting with
263:) linkages. Some
204:allylic oxidations
158:
52:structural formula
36:
2596:
2595:
2534:Sulfenyl chloride
2512:
2511:
2011:
2010:
1830:(only C, H and O)
1671:Functional groups
1623:10.1021/cr040170k
1591:978-0-470-84289-8
1576:. pp. 1–12.
1488:(16): 2201–2221.
1455:Organic Syntheses
1432:10.1021/cr1004474
1426:(12): 7774–7854.
1387:10.1021/cr1002744
1338:10.1021/cr400008h
1190:978-0-85404-190-9
1133:Organic Chemistry
976:terephthalic acid
907:allylic oxidation
827:
812:
803:
791:
775:
759:
750:
738:
697:
685:
674:
666:
658:
641:
621:
601:
581:
572:
555:
337:A representative
228:Pentadienyl group
222:Pentadienyl group
134:chemical reaction
40:organic chemistry
16:(Redirected from
2621:
2563:
2468:Trifluoromethoxy
2036:
2032:
1835:
1831:
1684:
1664:
1657:
1650:
1641:
1635:
1634:
1617:(9): 3800–3842.
1611:Chemical Reviews
1602:
1596:
1595:
1569:
1563:
1562:
1552:
1512:
1506:
1505:
1477:
1471:
1470:
1450:
1444:
1443:
1420:Chemical Reviews
1415:
1409:
1408:
1398:
1381:(3): 1846–1913.
1375:Chemical Reviews
1366:
1360:
1359:
1349:
1332:(7): 5595–5698.
1326:Chemical Reviews
1321:
1315:
1314:
1283:Chemical Reviews
1278:
1272:
1271:
1245:
1239:
1236:
1230:
1229:
1201:
1195:
1194:
1174:
1168:
1167:
1143:
1137:
1136:
1128:
1119:
1108:
938:selenium dioxide
838:
836:
835:
830:
828:
825:
820:
817:
810:
808:
801:
799:
796:
789:
783:
780:
773:
767:
764:
757:
755:
748:
746:
743:
736:
708:
706:
705:
700:
698:
695:
693:
690:
683:
672:
671:
664:
663:
656:
655:
649:
646:
639:
629:
626:
619:
609:
606:
599:
589:
586:
579:
577:
570:
569:
563:
560:
553:
509:
501:
396:
366:
361:
356:
351:
277:arachidonic acid
262:
238:
184:"has an allylic
183:
162:allylic position
121:
110:
99:Theodor Wertheim
96:
86:
76:) attached to a
75:
66:methylene bridge
63:
21:
2629:
2628:
2624:
2623:
2622:
2620:
2619:
2618:
2614:Allyl compounds
2599:
2598:
2597:
2592:
2561:
2553:
2508:
2463:Trichloromethyl
2458:Trifluoromethyl
2432:
2409:
2371:
2348:
2243:
2212:Phosphine oxide
2164:
2030:
2028:
2027:
2025:
2023:
2021:
2019:
2017:
2007:
1967:
1910:
1829:
1828:
1823:
1818:
1808:
1682:
1681:
1673:
1668:
1638:
1604:
1603:
1599:
1592:
1571:
1570:
1566:
1527:(7601): 77–81.
1514:
1513:
1509:
1479:
1478:
1474:
1452:
1451:
1447:
1417:
1416:
1412:
1368:
1367:
1363:
1323:
1322:
1318:
1280:
1279:
1275:
1260:
1247:
1246:
1242:
1237:
1233:
1203:
1202:
1198:
1191:
1176:
1175:
1171:
1145:
1144:
1140:
1130:
1129:
1122:
1109:
1100:
1096:
1039:
1008:
1004:
992:
990:Allyl compounds
959:
955:
951:
947:
923:sesquiterpenoid
903:
856:
848:epichlorohydrin
729:
728:
542:
541:
520:rancidification
507:
503:
500:
496:
489:
483:
471:
411:
394:
390:
386:
382:
375:
364:
359:
354:
350:
346:
316:rancidification
282:
260:
256:
237:
233:
230:
224:
181:
177:
173:
146:
120:
116:
112:
85:
81:
73:
69:
62:
58:
54:
28:
23:
22:
15:
12:
11:
5:
2627:
2625:
2617:
2616:
2611:
2609:Alkenyl groups
2601:
2600:
2594:
2593:
2591:
2590:
2589:
2588:
2583:
2571:
2564:
2558:
2555:
2554:
2552:
2551:
2549:Sulfinylamines
2546:
2541:
2536:
2531:
2529:Phosphoramides
2526:
2524:Isothiocyanate
2520:
2518:
2514:
2513:
2510:
2509:
2507:
2506:
2501:
2500:
2499:
2489:
2488:
2487:
2477:
2476:
2475:
2470:
2465:
2460:
2455:
2444:
2442:
2434:
2433:
2431:
2430:
2425:
2419:
2417:
2411:
2410:
2408:
2407:
2402:
2400:Selenenic acid
2397:
2395:Seleninic acid
2392:
2390:Selenonic acid
2387:
2381:
2379:
2373:
2372:
2370:
2369:
2364:
2358:
2356:
2350:
2349:
2347:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2311:
2306:
2301:
2296:
2291:
2286:
2281:
2276:
2271:
2270:
2269:
2259:
2253:
2251:
2245:
2244:
2242:
2241:
2236:
2231:
2226:
2225:
2224:
2214:
2209:
2204:
2199:
2198:
2197:
2187:
2186:
2185:
2183:Phosphodiester
2174:
2172:
2166:
2165:
2163:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2061:
2060:
2055:
2044:
2042:
2033:
2029:(one element,
2013:
2012:
2009:
2008:
2006:
2005:
2004:
2003:
1993:
1992:
1991:
1986:
1975:
1973:
1969:
1968:
1966:
1965:
1960:
1955:
1954:
1953:
1943:
1942:
1941:
1936:
1931:
1920:
1918:
1912:
1911:
1909:
1908:
1906:Methylenedioxy
1903:
1898:
1897:
1896:
1891:
1881:
1880:
1879:
1874:
1864:
1863:
1862:
1852:
1847:
1841:
1839:
1832:
1810:
1809:
1807:
1806:
1801:
1796:
1795:
1794:
1789:
1779:
1778:
1777:
1772:
1767:
1762:
1757:
1752:
1742:
1741:
1740:
1735:
1725:
1724:
1723:
1718:
1713:
1708:
1703:
1698:
1687:
1685:
1683:(only C and H)
1675:
1674:
1669:
1667:
1666:
1659:
1652:
1644:
1637:
1636:
1597:
1590:
1564:
1507:
1472:
1445:
1410:
1361:
1316:
1289:(1): 345–364.
1273:
1258:
1240:
1231:
1196:
1189:
1169:
1158:(3): 289–315.
1138:
1120:
1097:
1095:
1092:
1091:
1090:
1085:
1080:
1075:
1070:
1065:
1060:
1055:
1050:
1045:
1043:Allylic strain
1038:
1035:
1034:
1033:
1024:
1021:natural rubber
1010:
1006:
1002:
999:Crotyl alcohol
991:
988:
971:substituents.
961:
960:
957:
953:
949:
945:
902:
899:
855:
852:
840:
839:
824:
816:
807:
795:
787:
779:
771:
763:
754:
742:
714:allyl chloride
710:
709:
689:
680:
677:
670:
662:
654:
645:
636:
633:
625:
616:
613:
605:
596:
593:
585:
576:
568:
559:
550:
482:
479:
476:
475:
469:
449:
448:
410:
407:
374:
371:
301:leaf aldehydes
289:hydroperoxides
280:
273:linolenic acid
241:doubly allylic
226:Main article:
223:
220:
186:hydroxyl group
145:
142:
124:allyl chloride
105:and named it "
94:Allium sativum
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2626:
2615:
2612:
2610:
2607:
2606:
2604:
2587:
2584:
2582:
2579:
2578:
2577:
2576:
2572:
2570:
2569:
2565:
2560:
2559:
2556:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2521:
2519:
2515:
2505:
2502:
2498:
2495:
2494:
2493:
2490:
2486:
2483:
2482:
2481:
2478:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2450:
2449:
2446:
2445:
2443:
2441:
2440:
2435:
2429:
2428:Telluroketone
2426:
2424:
2421:
2420:
2418:
2416:
2412:
2406:
2403:
2401:
2398:
2396:
2393:
2391:
2388:
2386:
2383:
2382:
2380:
2378:
2374:
2368:
2365:
2363:
2360:
2359:
2357:
2355:
2351:
2345:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2314:Sulfonic acid
2312:
2310:
2307:
2305:
2304:Sulfinic acid
2302:
2300:
2299:Thiosulfonate
2297:
2295:
2292:
2290:
2289:Thiosulfinate
2287:
2285:
2284:Sulfenic acid
2282:
2280:
2277:
2275:
2272:
2268:
2265:
2264:
2263:
2260:
2258:
2255:
2254:
2252:
2250:
2246:
2240:
2239:Phosphaallene
2237:
2235:
2234:Phosphaalkyne
2232:
2230:
2229:Phosphaalkene
2227:
2223:
2220:
2219:
2218:
2215:
2213:
2210:
2208:
2205:
2203:
2200:
2196:
2193:
2192:
2191:
2188:
2184:
2181:
2180:
2179:
2176:
2175:
2173:
2171:
2167:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2059:
2056:
2054:
2051:
2050:
2049:
2046:
2045:
2043:
2041:
2037:
2034:
2014:
2002:
1999:
1998:
1997:
1994:
1990:
1987:
1985:
1982:
1981:
1980:
1977:
1976:
1974:
1970:
1964:
1961:
1959:
1956:
1952:
1949:
1948:
1947:
1944:
1940:
1937:
1935:
1932:
1930:
1927:
1926:
1925:
1922:
1921:
1919:
1917:
1913:
1907:
1904:
1902:
1901:Ethylenedioxy
1899:
1895:
1892:
1890:
1887:
1886:
1885:
1882:
1878:
1875:
1873:
1870:
1869:
1868:
1865:
1861:
1858:
1857:
1856:
1853:
1851:
1848:
1846:
1843:
1842:
1840:
1836:
1833:
1827:
1821:
1816:
1811:
1805:
1802:
1800:
1797:
1793:
1790:
1788:
1785:
1784:
1783:
1780:
1776:
1773:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1747:
1746:
1743:
1739:
1736:
1734:
1731:
1730:
1729:
1726:
1722:
1719:
1717:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1693:
1692:
1689:
1688:
1686:
1680:
1676:
1672:
1665:
1660:
1658:
1653:
1651:
1646:
1645:
1642:
1632:
1628:
1624:
1620:
1616:
1612:
1608:
1601:
1598:
1593:
1587:
1583:
1579:
1575:
1568:
1565:
1560:
1556:
1551:
1546:
1542:
1538:
1534:
1530:
1526:
1522:
1518:
1511:
1508:
1503:
1499:
1495:
1491:
1487:
1483:
1476:
1473:
1468:
1464:
1460:
1456:
1449:
1446:
1441:
1437:
1433:
1429:
1425:
1421:
1414:
1411:
1406:
1402:
1397:
1392:
1388:
1384:
1380:
1376:
1372:
1365:
1362:
1357:
1353:
1348:
1343:
1339:
1335:
1331:
1327:
1320:
1317:
1312:
1308:
1304:
1300:
1296:
1292:
1288:
1284:
1277:
1274:
1269:
1265:
1261:
1255:
1251:
1244:
1241:
1235:
1232:
1227:
1223:
1219:
1215:
1211:
1207:
1200:
1197:
1192:
1186:
1182:
1181:
1173:
1170:
1165:
1161:
1157:
1153:
1149:
1142:
1139:
1134:
1127:
1125:
1121:
1117:
1116:0-471-60180-2
1113:
1107:
1105:
1103:
1099:
1093:
1089:
1086:
1084:
1081:
1079:
1076:
1074:
1071:
1069:
1066:
1064:
1061:
1059:
1056:
1054:
1051:
1049:
1046:
1044:
1041:
1040:
1036:
1032:
1028:
1025:
1022:
1018:
1014:
1011:
1000:
997:
996:
995:
989:
987:
985:
981:
977:
972:
970:
966:
956:C=CR'-C(OH)R"
943:
942:
941:
939:
930:
926:
924:
920:
916:
912:
908:
900:
894:
890:
888:
884:
880:
875:
873:
869:
865:
861:
853:
851:
849:
845:
844:allyl alcohol
822:
814:
805:
793:
777:
769:
761:
752:
740:
727:
726:
725:
723:
719:
715:
687:
678:
675:
668:
660:
652:
643:
634:
623:
614:
611:
603:
594:
591:
583:
574:
566:
557:
548:
540:
539:
538:
536:
532:
528:
527:acrylonitrile
523:
521:
517:
513:
494:
488:
480:
478:
466:
462:
461:
460:
458:
454:
444:
440:
436:
435:
434:
432:
428:
424:
420:
416:
408:
402:
398:
380:
372:
367:
357:
355:linoleic acid
344:
340:
335:
331:
329:
325:
321:
317:
313:
308:
306:
302:
298:
294:
290:
286:
278:
274:
270:
269:linoleic acid
266:
254:
250:
246:
242:
229:
221:
219:
217:
213:
209:
208:ene reactions
205:
201:
197:
195:
191:
187:
171:
167:
163:
155:
150:
143:
141:
139:
135:
131:
127:
125:
109:
108:Schwefelallyl
104:
100:
95:
90:
79:
67:
53:
49:
45:
41:
32:
19:
2573:
2566:
2480:Vinyl halide
2437:
2367:Borinic acid
2362:Boronic acid
2339:Thioxanthate
1754:
1679:Hydrocarbons
1614:
1610:
1606:
1600:
1573:
1567:
1524:
1520:
1510:
1485:
1481:
1475:
1458:
1454:
1448:
1423:
1419:
1413:
1378:
1374:
1364:
1329:
1325:
1319:
1286:
1282:
1276:
1249:
1243:
1234:
1209:
1205:
1199:
1179:
1172:
1155:
1151:
1141:
1132:
993:
980:benzoic acid
973:
962:
935:
906:
904:
876:
857:
841:
718:chlorination
711:
531:ammoxidation
524:
502:groups into
490:
477:
451:In terms of
450:
412:
378:
376:
339:triglyceride
312:autoxidation
309:
305:antifeedants
240:
231:
198:
188:". Allylic
169:
166:allylic site
165:
161:
159:
154:free radical
144:Nomenclature
129:
128:
43:
37:
2544:Thiocyanate
2539:Sulfonamide
2504:Perchlorate
2492:Acyl halide
2453:Fluoroethyl
2334:Thionoester
2222:Phosphonium
2207:Phosphinate
2202:Phosphonous
2190:Phosphonate
1889:Hydroperoxy
1711:Cyclopropyl
1347:10045/38276
1212:: 275–297.
516:linseed oil
512:drying oils
379:homoallylic
373:Homoallylic
343:linseed oil
320:drying oils
97:. In 1844,
78:vinyl group
48:substituent
44:allyl group
2603:Categories
2448:Haloalkane
2319:Thioketone
2274:Persulfide
2170:Phosphorus
2135:Isocyanate
2125:Isonitrile
2026:or oxygen
2024:hydrogen,
2020:not being
2001:Orthoester
1894:Dioxiranes
1872:Enol ether
1760:1-Propenyl
1259:0471980501
1094:References
1078:Acetylenic
1029:, such as
948:C=CR'-CHR"
915:grapefruit
911:nootkatone
854:Allylation
485:See also:
457:MO diagram
365:oleic acid
324:oil paints
293:jasmonates
253:pentadiene
210:, and the
130:Allylation
103:garlic oil
2581:inorganic
2415:Tellurium
2329:Thioester
2294:Sulfoxide
2279:Disulfide
2267:Sulfonium
2217:Phosphine
2195:Phosphite
2178:Phosphate
2110:Carbamate
2085:Hydrazone
2018:element,
2016:Only one
1989:Anhydride
1728:Methylene
1502:196767407
1482:Synthesis
1311:218617434
919:valencene
901:Oxidation
860:carbanion
786:⟶
722:propylene
669:≡
661:−
632:⟶
567:−
453:MO theory
377:The term
341:found in
328:varnishes
249:oxidation
190:C−H bonds
138:substrate
50:with the
2562:See also
2497:Chloride
2423:Tellurol
2377:Selenium
2344:Xanthate
2058:Ammonium
2040:Nitrogen
2022:carbon,
1979:Carboxyl
1946:Aldehyde
1934:Acryloyl
1916:carbonyl
1820:hydrogen
1775:Cumulene
1631:17848093
1559:27096371
1440:21923136
1405:21235271
1356:23540914
1303:32396335
1268:64-25218
1226:12221977
1083:Naloxone
1068:Benzylic
1037:See also
1017:terpenes
1005:CH=CH−CH
952:+ → R
514:such as
415:radicals
216:Benzylic
200:Benzylic
172:. Thus,
2586:organic
2385:Selenol
2309:Sulfone
2262:Sulfide
2160:NONOate
2155:Nitroso
2145:Nitrite
2140:Nitrate
2130:Cyanate
2120:Nitrile
2105:Amidine
2100:Imidate
2070:Nitrene
2065:Hydrazo
2053:Enamine
1984:Acetoxy
1972:carboxy
1939:Benzoyl
1877:Epoxide
1860:Methoxy
1850:Alcohol
1804:Carbene
1738:Methine
1550:4860034
1529:Bibcode
1396:3116714
1073:Vinylic
917:, from
535:propene
423:cations
409:Bonding
352:sites (
170:allylic
132:is any
117:C=CH−CH
18:Allylic
2485:Iodide
2405:Selone
2249:Sulfur
1958:Ketone
1951:Ketene
1929:Acetyl
1884:Peroxy
1855:Alkoxy
1845:Acetal
1826:oxygen
1815:carbon
1799:Alkyne
1792:Benzyl
1787:Phenyl
1770:Allene
1765:Crotyl
1745:Alkene
1733:Bridge
1721:Pentyl
1706:Propyl
1696:Methyl
1629:
1588:
1557:
1547:
1521:Nature
1500:
1461:: 86.
1438:
1403:
1393:
1354:
1309:
1301:
1266:
1256:
1224:
1187:
1114:
982:, and
885:. The
455:, the
421:, and
419:anions
299:, and
275:, and
257:C=C−CH
243:. The
89:garlic
82:−CH=CH
59:−HC=CH
2517:Other
2354:Boron
2324:Thial
2257:Thiol
2150:Nitro
2115:Imide
2095:Amide
2080:Oxime
2075:Imine
2048:Amine
1996:Ester
1963:Ynone
1867:Ether
1838:R-O-R
1813:Only
1755:Allyl
1750:Vinyl
1716:Butyl
1701:Ethyl
1691:Alkyl
1498:S2CID
1307:S2CID
965:alkyl
883:enone
387:=CHCH
178:=CHCH
46:is a
42:, an
2439:Halo
1924:Acyl
1824:and
1782:Aryl
1627:PMID
1586:ISBN
1555:PMID
1436:PMID
1401:PMID
1352:PMID
1299:PMID
1264:LCCN
1254:ISBN
1222:PMID
1185:ISBN
1112:ISBN
969:aryl
925::
846:and
790:ClCH
504:CH−S
358:and
326:and
271:, α-
261:−C=C
152:The
2090:Azo
1619:doi
1615:107
1578:doi
1545:PMC
1537:doi
1525:533
1490:doi
1463:doi
1428:doi
1424:111
1391:PMC
1383:doi
1379:111
1342:hdl
1334:doi
1330:113
1291:doi
1287:121
1214:doi
1160:doi
1009:OH)
1001:(CH
967:or
826:HCl
720:of
533:of
529:by
508:−CH
214:.
164:or
70:−CH
55:−CH
38:In
2605::
1822:,
1817:,
1625:.
1613:.
1607:N-
1584:.
1553:.
1543:.
1535:.
1523:.
1519:.
1496:.
1486:45
1484:.
1459:62
1457:.
1434:.
1422:.
1399:.
1389:.
1377:.
1373:.
1350:.
1340:.
1328:.
1305:.
1297:.
1285:.
1262:.
1220:.
1210:53
1208:.
1156:51
1154:.
1150:.
1123:^
1101:^
986:.
978:,
874:.
850:.
811:CH
802:CH
774:Cl
758:CH
749:CH
737:CH
724::
657:CH
640:CH
600:NH
580:CH
571:CH
554:CH
522:.
497:CH
417:,
395:Cl
391:CH
383:CH
347:CH
330:.
295:,
234:CH
232:A
206:,
194:sp
182:OH
174:CH
140:.
126:.
91:,
1663:e
1656:t
1649:v
1633:.
1621::
1594:.
1580::
1561:.
1539::
1531::
1504:.
1492::
1469:.
1465::
1442:.
1430::
1407:.
1385::
1358:.
1344::
1336::
1313:.
1293::
1270:.
1228:.
1216::
1193:.
1166:.
1162::
1118:.
1023:.
1007:2
1003:3
958:2
954:2
950:2
946:2
944:R
823:+
815:2
806:=
794:2
778:2
770:+
762:2
753:=
741:3
696:O
688:2
684:H
679:6
676:+
673:N
665:C
653:=
644:2
635:2
624:2
620:O
615:3
612:+
604:3
595:2
592:+
584:2
575:=
558:3
549:2
506:x
499:2
470:2
393:2
389:2
385:2
368:)
349:2
281:2
259:2
255:(
236:2
180:2
176:2
119:2
115:2
113:H
84:2
80:(
74:−
72:2
68:(
61:2
57:2
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
