402:
90:
471:
71:
20:
420:
938:
Walther, Dirk; Stollenz, Michael; Görls, Helmar (2001). "Dinuclear [RNi(oxam)NiR] Complexes (Oxam = N1,N2-bis(2-pyridylmethyl)-N3,N4-bis(2,4,6-trimethylphenyl)oxalamidinate; R = Me, Ph, CâźCH, CâźCPH): Reactions of the Methyl
Complex and Formation of [Li(THF)]2Li2Ni2Me8 and
914:
Hay-Motherwell, Robyn S.; Wilkinson, Geoffrey; Hussain, Bilquis; Hursthouse, Michael B. (1989). "Homoleptic methyl compounds of rhodium and iridium(III). X-Ray crystal structures of tetramethylethylenediamine lithium hexamethyl-rhodate(III) and -iridate(III)".
753:
Morris, Robert J.; Girolami, Gregory S. (1988). "Permethylmanganates. Synthesis and characterization of divalent [MnMe42-], trivalent [MnMe52-], and tetravalent [MnMe62-]".
459:
One determinant of the kinetic stability of metal-alkyl complexes is the presence of hydrogen at the position beta to the metal. If such hydrogens are present and if the metal center is
1648:
1685:
456:
between a C-H bond on the alkyl group and the metal. Such interactions are especially common for complexes of early transition metals in their highest oxidation states.
1189:
1535:
703:
Morse, Paige M.; Girolami, Gregory S. (1989). "Are d0 ML6 complexes always octahedral? The x-ray structure of trigonal-prismatic [Li(tmed)]2[ZrMe6]".
341:
Metal alkyl complexes are prepared generally by two pathways, use of alkyl nucleophiles and use of alkyl electrophiles. Nucleophilic sources of alkyl ligands include
1715:
1752:
788:
Morris, Robert J.; Girolami, Gregory S. (1991). "High-valent organomanganese chemistry. 1. Synthesis and characterization of manganese(III) and -(IV) alkyls".
1771:
1842:
1566:
349:. Since many strong nucleophiles are also potent reductants, mildly nucleophilic alkylating agents are sometimes employed to avoid redox reactions.
619:
1707:
1515:
1386:
559:
531:
365:
979:
684:
1821:
1672:
1593:
1540:
1182:
599:
1558:
1510:
1833:
1788:
1744:
1728:
1530:
1497:
1487:
1374:
817:"Isolation and Characterization of a Tetramethyliron(III) Ferrate: An Intermediate in the Reduction Pathway of Ferric Salts with MeMg
1910:
1874:
1783:
1640:
1439:
998:"X-ray Crystal Structures and the Facile Oxidative (AuâC) Cleavage of the Dimethylaurate(I) and Tetramethylaurate(III) Homologues"
1736:
1699:
1694:
1660:
1502:
1451:
1416:
1399:
1391:
1327:
1905:
1545:
1318:
1306:
1277:
1272:
1175:
1621:
1525:
1479:
1362:
1282:
1236:
997:
1294:
1136:
Forbes, Jeffrey G.; Gellman, Andrew J. (1993-07-01). "The .beta.-hydride elimination mechanism in adsorbed alkyl groups".
57:
complexes. Indeed, the first reported example of a complex containing a metal-sp carbon bond was the homoleptic complex
1813:
1635:
1349:
613:
John Bacsa; Felix Hanke; Sarah
Hindley; Rajesh Odedra; George R. Darling; Anthony C. Jones; Alexander Steiner (2011).
1056:"Evidence for CarbonâHydrogenâTitanium Interactions: Synthesis and Crystal Structures of the Agostic alkyls [TiCl
74:
Structure of diethylzinc. The Zn-C bonds measure 194.8(5) pm, while the C-Zn-C angle is slightly bent with 176.2(4)°.
53:
Most metal alkyl complexes contain other, non-alkyl ligands. Great interest, mainly theoretical, has focused on the
401:
460:
1797:
1357:
1212:
1027:
King, B. (1970). "Applications of Metal
Carbonyl Anions in the Synthesis of Unusual Organometallic Compounds".
464:
360:
Electrophilic alkylation commonly starts with low valence metal complexes. Typical electrophilic reagents are
354:
1585:
1054:
Z. Dawoodi; M. L. H. Green; V. S. B. Mtetwa; K. Prout; A. J. Schultz; J. M. Williams; T. F. Koetzle (1986).
502:
1680:
1492:
346:
1520:
498:
870:"Isolation and Characterization of a Homoleptic Tetramethylcobalt(III) Distorted Square-Planar Complex"
1471:
1198:
486:
31:
1861:
89:
1879:
671:
Kleinhenz, Sven; Seppelt, Konrad (1999). "Preparation and
Structures of Methyltitanium Compounds".
453:
440:
350:
1884:
1866:
1612:
1217:
891:
393:
188:
93:
62:
409:
1153:
1118:
850:
815:
Al-Afyouni, Malik H.; Fillman, Kathlyn L.; Brennessel, William W.; Neidig, Michael L. (2014).
770:
646:
555:
527:
1145:
1110:
1083:
1036:
1009:
975:
948:
920:
881:
840:
832:
797:
762:
735:
712:
680:
636:
628:
595:
586:
Kleinhenz, S.; Pfennig, V.; Seppelt, K. (1998). "Preparation and
Structures of , , , and ".
494:
342:
35:
966:
Wyrwa, R.; Görls, H. (1999). "Ungewöhnliche MolekĂŒlstrukturen fĂŒr Platin(II)-at-Komplexe".
470:
318:
301:
1630:
1344:
1101:
Scherer, W.; McGrady, G. S. (2004). "Agostic
Interactions in d Metal Alkyl Complexes".
845:
816:
641:
614:
477:
These conversions are assumed to proceed via the intermediacy of agostic interactions.
45:. Such complexes are not only pervasive but are of practical and theoretical interest.
1899:
1339:
1244:
895:
490:
413:
730:
Beatrice
Roessler; Sven Kleinhenza; Konrad Seppelt (2000). "Pentamethylmolybdenum".
80:
Mixed ligand, or heteroleptic, complexes containing alkyls are numerous. In nature,
70:
361:
284:
886:
869:
19:
96:
is an example of a "homoleptic" (all ligands being the same) metal alkyl complex.
1404:
81:
58:
980:
10.1002/(SICI)1521-3749(199911)625:11<1904::AID-ZAAC1904>3.0.CO;2-2
685:
10.1002/(SICI)1521-3765(19991203)5:12<3573::AID-CHEM3573>3.3.CO;2-F
600:
10.1002/(SICI)1521-3765(19980904)4:9<1687::AID-CHEM1687>3.0.CO;2-R
54:
1157:
868:
Carpenter, Stephanie H.; Brennessel, William W.; Neidig, Michael L. (2019).
1122:
1114:
854:
774:
650:
632:
1167:
1087:
924:
1149:
1040:
801:
766:
716:
526:(3., completely rev. and extended ed.). Weinheim: Wiley-VCH-Verl.
1013:
952:
909:
907:
905:
836:
489:
operate via the intermediacy of metal alkyls. These reactions include
739:
698:
696:
694:
42:
1055:
419:
418:
88:
39:
436:
1171:
364:. Illustrative is the preparation of the methyl derivative of
991:
989:
615:"The Solid State Structures of Dimethylzinc and Diethylzinc"
469:
552:
Organotransition Metal
Chemistry, from Bonding to Catalysis
84:
and its many derivatives contain reactive Co-alkyl bonds.
996:
Zhu, Dunming; Lindeman, Sergey V.; Kochi, Jay K. (1999).
23:
Vitamin B12 is a naturally occurring metal-alkyl complex.
917:
Journal of the
Chemical Society, Chemical Communications
1854:
1764:
1605:
1578:
1464:
1432:
1260:
1229:
1205:
968:Zeitschrift fĂŒr Anorganische und Allgemeine Chemie
522:Oliveira, José; Elschenbroich, Christoph (2006).
448:Agostic interactions and beta-hydride elimination
65:, tetramethyltitanium, and tetranorbornylcobalt.
443:between the methyl group and the Ti(IV) center.
1183:
8:
666:
664:
662:
660:
1190:
1176:
1168:
505:reactions also involve metal-alkyl bonds.
885:
844:
640:
581:
579:
577:
575:
573:
571:
545:
543:
1138:Journal of the American Chemical Society
825:Journal of the American Chemical Society
755:Journal of the American Chemical Society
705:Journal of the American Chemical Society
501:. It is assumed that the corresponding
101:
69:
18:
620:Angewandte Chemie International Edition
514:
554:. New York: University Science Books.
366:cyclopentadienyliron dicarbonyl anion
7:
392:Many metal alkyls are prepared by
14:
423:Structure of the alkyl complex (C
126:only observed as monoetherate, d
103:Homoleptic metal alkyl complexes
467:to form a metal-alkene complex:
408:An example is the reaction of a
400:
140:one bridging methyl ligand, d,d
28:Transition metal alkyl complexes
463:, then the complex can undergo
673:Chemistry - A European Journal
588:Chemistry â A European Journal
34:that contain a bond between a
1:
887:10.1021/acs.organomet.9b00387
1080:J. Chem. Soc., Dalton Trans.
497:, alkene isomerization, and
939:[Li(THF)]4Ni2Me8".
230:low-spin, d, square planar
1927:
461:coordinatively unsaturated
452:Some metal alkyls feature
357:are such milder reagents.
61:. Other examples include
355:organoaluminium compounds
1911:Organometallic chemistry
465:beta-hydride elimination
133:trigonal bipyramidal, d
1076:)R] (R = Et or Me)"
732:Chemical Communications
550:Hartwig, J. F. (2010).
347:organolithium compounds
1906:Coordination chemistry
1199:Coordination complexes
1115:10.1002/anie.200200548
633:10.1002/anie.201105099
474:
444:
200:trigonal prismatic, d
154:trigonal prismatic, d
147:trigonal prismatic, d
97:
75:
32:coordination complexes
24:
499:olefin polymerization
487:homogeneous catalysts
473:
422:
92:
73:
22:
1103:Angew. Chem. Int. Ed
1088:10.1039/dt9860001629
925:10.1039/C39890001436
454:agostic interactions
351:Organozinc compounds
16:Coordination complex
1150:10.1021/ja00067a048
1041:10.1021/ar50036a004
831:(44): 15457â15460.
802:10.1021/om00049a047
767:10.1021/ja00226a049
717:10.1021/ja00193a061
627:(49): 11685â11687.
441:agostic interaction
439:), highlighting an
104:
475:
445:
394:oxidative addition
102:
98:
94:Hexamethyltungsten
76:
63:hexamethyltungsten
25:
1893:
1892:
1144:(14): 6277â6283.
1109:(14): 1782â1806.
1014:10.1021/om990043s
1008:(11): 2241â2248.
974:(11): 1904â1907.
953:10.1021/om000960u
947:(20): 4221â4229.
880:(19): 3486â3489.
837:10.1021/ja5080757
761:(18): 6245â6246.
734:(12): 1039â1040.
711:(11): 4114â4116.
679:(12): 3573â3580.
561:978-1-891389-53-5
533:978-3-527-29390-2
343:Grignard reagents
334:
333:
237:square planar, d
1918:
1192:
1185:
1178:
1169:
1162:
1161:
1133:
1127:
1126:
1098:
1092:
1091:
1051:
1045:
1044:
1024:
1018:
1017:
993:
984:
983:
963:
957:
956:
935:
929:
928:
911:
900:
899:
889:
865:
859:
858:
848:
812:
806:
805:
785:
779:
778:
750:
744:
743:
740:10.1039/b000987n
727:
721:
720:
700:
689:
688:
668:
655:
654:
644:
610:
604:
603:
594:(9): 1687â1691.
583:
566:
565:
547:
538:
537:
519:
495:hydroformylation
404:
105:
36:transition metal
1926:
1925:
1921:
1920:
1919:
1917:
1916:
1915:
1896:
1895:
1894:
1889:
1870:
1850:
1837:
1829:
1825:
1817:
1809:
1805:
1801:
1792:
1779:
1775:
1760:
1756:
1748:
1740:
1732:
1723:
1719:
1711:
1703:
1689:
1676:
1668:
1664:
1656:
1652:
1644:
1625:
1616:
1601:
1597:
1589:
1574:
1562:
1553:
1549:
1506:
1483:
1475:
1460:
1455:
1447:
1443:
1428:
1424:
1420:
1412:
1408:
1395:
1382:
1378:
1370:
1366:
1353:
1335:
1331:
1322:
1314:
1310:
1302:
1298:
1290:
1286:
1256:
1252:
1248:
1240:
1225:
1221:
1201:
1196:
1166:
1165:
1135:
1134:
1130:
1100:
1099:
1095:
1075:
1071:
1067:
1063:
1059:
1053:
1052:
1048:
1035:(12): 417â427.
1026:
1025:
1021:
1002:Organometallics
995:
994:
987:
965:
964:
960:
941:Organometallics
937:
936:
932:
913:
912:
903:
874:Organometallics
867:
866:
862:
814:
813:
809:
790:Organometallics
787:
786:
782:
752:
751:
747:
729:
728:
724:
702:
701:
692:
670:
669:
658:
612:
611:
607:
585:
584:
569:
562:
549:
548:
541:
534:
524:Organometallics
521:
520:
516:
511:
483:
450:
434:
430:
426:
410:Vaska's complex
387:
383:
379:
375:
339:
326:
322:
309:
305:
292:
288:
196:
192:
180:
176:
123:
119:
51:
17:
12:
11:
5:
1924:
1922:
1914:
1913:
1908:
1898:
1897:
1891:
1890:
1888:
1887:
1882:
1877:
1872:
1868:
1864:
1858:
1856:
1855:Halide donors:
1852:
1851:
1849:
1848:
1840:
1835:
1831:
1827:
1823:
1819:
1815:
1811:
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1766:
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1759:
1758:
1754:
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1746:
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1713:
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1701:
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1646:
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1633:
1628:
1623:
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1609:
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1603:
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1599:
1595:
1591:
1587:
1582:
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1576:
1575:
1573:
1572:
1564:
1560:
1556:
1551:
1547:
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1538:
1533:
1528:
1523:
1518:
1513:
1508:
1504:
1500:
1495:
1490:
1485:
1481:
1477:
1473:
1468:
1466:
1462:
1461:
1459:
1458:
1453:
1449:
1445:
1441:
1436:
1434:
1430:
1429:
1427:
1426:
1422:
1418:
1414:
1410:
1406:
1402:
1397:
1393:
1389:
1384:
1380:
1376:
1372:
1368:
1364:
1360:
1355:
1351:
1347:
1342:
1337:
1333:
1329:
1325:
1320:
1316:
1312:
1308:
1304:
1300:
1296:
1292:
1288:
1284:
1280:
1275:
1270:
1264:
1262:
1258:
1257:
1255:
1254:
1250:
1246:
1242:
1238:
1233:
1231:
1227:
1226:
1224:
1223:
1219:
1215:
1209:
1207:
1203:
1202:
1197:
1195:
1194:
1187:
1180:
1172:
1164:
1163:
1128:
1093:
1073:
1069:
1065:
1061:
1057:
1046:
1029:Acc. Chem. Res
1019:
985:
958:
930:
901:
860:
807:
796:(3): 792â799.
780:
745:
722:
690:
656:
605:
567:
560:
539:
532:
513:
512:
510:
507:
482:
479:
449:
446:
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428:
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405:
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385:
381:
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156:
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149:
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145:
142:
141:
138:
135:
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128:
127:
124:
121:
117:
113:
112:
109:
100:
99:
78:
77:
50:
47:
15:
13:
10:
9:
6:
4:
3:
2:
1923:
1912:
1909:
1907:
1904:
1903:
1901:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1865:
1863:
1860:
1859:
1857:
1853:
1847:
1846:
1841:
1839:
1832:
1830:
1820:
1818:
1812:
1810:
1796:
1794:
1787:
1785:
1782:
1780:
1770:
1769:
1767:
1763:
1757:
1751:
1749:
1743:
1741:
1735:
1733:
1727:
1725:
1714:
1712:
1706:
1704:
1698:
1696:
1693:
1691:
1684:
1682:
1679:
1677:
1671:
1669:
1659:
1657:
1647:
1645:
1639:
1637:
1634:
1632:
1629:
1627:
1620:
1618:
1611:
1610:
1608:
1604:
1598:
1592:
1590:
1584:
1583:
1581:
1577:
1571:
1569:
1565:
1563:
1557:
1555:
1544:
1542:
1539:
1537:
1534:
1532:
1529:
1527:
1524:
1522:
1519:
1517:
1514:
1512:
1509:
1507:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1478:
1476:
1470:
1469:
1467:
1463:
1457:
1450:
1448:
1438:
1437:
1435:
1431:
1425:
1415:
1413:
1403:
1401:
1398:
1396:
1390:
1388:
1385:
1383:
1373:
1371:
1361:
1359:
1356:
1354:
1348:
1346:
1343:
1341:
1338:
1336:
1326:
1324:
1317:
1315:
1305:
1303:
1293:
1291:
1281:
1279:
1276:
1274:
1271:
1269:
1266:
1265:
1263:
1259:
1253:
1243:
1241:
1235:
1234:
1232:
1228:
1222:
1216:
1214:
1211:
1210:
1208:
1204:
1200:
1193:
1188:
1186:
1181:
1179:
1174:
1173:
1170:
1159:
1155:
1151:
1147:
1143:
1139:
1132:
1129:
1124:
1120:
1116:
1112:
1108:
1104:
1097:
1094:
1089:
1085:
1081:
1077:
1050:
1047:
1042:
1038:
1034:
1030:
1023:
1020:
1015:
1011:
1007:
1003:
999:
992:
990:
986:
981:
977:
973:
969:
962:
959:
954:
950:
946:
942:
934:
931:
926:
922:
918:
910:
908:
906:
902:
897:
893:
888:
883:
879:
875:
871:
864:
861:
856:
852:
847:
842:
838:
834:
830:
826:
822:
820:
811:
808:
803:
799:
795:
791:
784:
781:
776:
772:
768:
764:
760:
756:
749:
746:
741:
737:
733:
726:
723:
718:
714:
710:
706:
699:
697:
695:
691:
686:
682:
678:
674:
667:
665:
663:
661:
657:
652:
648:
643:
638:
634:
630:
626:
622:
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568:
563:
557:
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529:
525:
518:
515:
508:
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504:
503:heterogeneous
500:
496:
492:
491:hydrogenation
488:
480:
478:
472:
468:
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457:
455:
447:
442:
438:
421:
417:
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414:methyl iodide
411:
403:
399:
398:
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395:
371:
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363:
362:alkyl halides
358:
356:
352:
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48:
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37:
33:
29:
21:
1844:
1567:
1267:
1141:
1137:
1131:
1106:
1102:
1096:
1079:
1049:
1032:
1028:
1022:
1005:
1001:
971:
967:
961:
944:
940:
933:
919:(19): 1436.
916:
877:
873:
863:
828:
824:
818:
810:
793:
789:
783:
758:
754:
748:
731:
725:
708:
704:
676:
672:
624:
618:
608:
591:
587:
551:
523:
517:
484:
476:
458:
451:
407:
391:
380:I â CpFe(CO)
359:
340:
79:
52:
27:
26:
1082:(8): 1629.
337:Preparation
82:vitamin B12
59:diethylzinc
1900:Categories
1516:amino acid
1433:Si donors:
509:References
55:homoleptic
1765:S donors:
1606:O donors:
1579:P donors:
1541:porphyrin
1488:imidazole
1465:N donors:
1261:C donors:
1230:B donors:
1206:H donors:
1158:0002-7863
896:203144530
481:Catalysis
1123:15054779
855:25333789
775:22148809
651:21919175
372:CpFe(CO)
111:comment
1379:& C
846:4227835
642:3326375
376:Na + CH
108:example
38:and an
1287:ïŒCH-CH
1156:
1121:
894:
853:
843:
773:
649:
639:
558:
530:
43:ligand
1278:HC(O)
1273:RC(O)
892:S2CID
485:Many
431:)TiCl
412:with
388:+ NaI
319:Hg(CH
302:Cd(CH
285:Zn(CH
173:Mo(CH
116:Ti(CH
49:Scope
40:alkyl
1681:acac
1653:/HCO
1536:bipy
1295:C(CH
1154:ISSN
1119:PMID
851:PMID
771:PMID
647:PMID
556:ISBN
528:ISBN
437:dmpe
396::
353:and
345:and
189:W(CH
30:are
1776:NCS
1753:OPR
1729:OSR
1708:ClO
1695:ONO
1673:RCO
1550:Si)
1546:(Me
1531:RCN
1498:RNO
1446:4ân
1444:SiR
1400:âĄCR
1392:=CR
1387:RNC
1311:ïŒCH
1146:doi
1142:115
1111:doi
1084:doi
1072:PMe
1064:PCH
1060:(Me
1037:doi
1010:doi
976:doi
972:625
949:doi
921:doi
882:doi
841:PMC
833:doi
829:136
798:doi
763:doi
759:110
736:doi
713:doi
709:111
681:doi
637:PMC
629:doi
596:doi
1902::
1880:Br
1875:Cl
1843:NC
1834:SR
1814:SO
1784:RS
1745:PO
1737:SO
1724:NO
1700:NO
1690:CO
1649:CO
1631:RO
1594:PR
1586:PR
1570:CS
1526:RN
1511:py
1503:NO
1493:NO
1472:NH
1456:Si
1381:70
1377:60
1350:CO
1345:CO
1340:CN
1319:RC
1307:CH
1283:CH
1237:BR
1152:.
1140:.
1117:.
1107:43
1105:.
1078:.
1068:CH
1031:.
1006:18
1004:.
1000:.
988:^
970:.
945:20
943:.
904:^
890:.
878:38
876:.
872:.
849:.
839:.
827:.
823:.
819:Br
794:10
792:.
769:.
757:.
707:.
693:^
675:.
659:^
645:.
635:.
625:50
623:.
617:.
590:.
570:^
542:^
493:,
416:.
384:CH
368::
330:d
313:d
296:d
279:d
272:d
265:d
258:d
251:d
244:d
223:d
216:d
213:2-
208:d
205:2-
183:d
168:d
161:d
1885:I
1869:2
1867:F
1862:F
1845:S
1838:O
1836:2
1828:3
1826:O
1824:2
1822:S
1816:2
1808:2
1806:S
1804:2
1802:C
1800:2
1798:R
1793:S
1791:2
1789:R
1778:2
1774:2
1772:R
1755:3
1747:4
1739:4
1731:2
1722:5
1720:H
1718:5
1716:C
1710:4
1702:3
1688:2
1686:R
1675:2
1667:4
1665:O
1663:2
1661:C
1655:3
1651:3
1643:2
1641:O
1636:O
1626:O
1624:2
1622:R
1617:O
1615:2
1613:H
1596:2
1588:3
1568:N
1561:2
1559:N
1554:N
1552:2
1548:3
1521:N
1505:2
1482:3
1480:N
1474:3
1454:3
1452:R
1442:n
1440:H
1423:7
1421:H
1419:9
1417:C
1411:5
1409:H
1407:5
1405:C
1394:2
1375:C
1369:6
1367:R
1365:6
1363:C
1358:C
1352:2
1334:4
1332:H
1330:6
1328:C
1323:R
1321:2
1313:2
1309:2
1301:3
1299:)
1297:2
1289:2
1285:2
1268:R
1251:n
1249:H
1247:m
1245:B
1239:2
1220:2
1218:H
1213:H
1191:e
1184:t
1177:v
1160:.
1148::
1125:.
1113::
1090:.
1086::
1074:2
1070:2
1066:2
1062:2
1058:3
1043:.
1039::
1033:3
1016:.
1012::
982:.
978::
955:.
951::
927:.
923::
898:.
884::
857:.
835::
821:"
804:.
800::
777:.
765::
742:.
738::
719:.
715::
687:.
683::
677:5
653:.
631::
602:.
598::
592:4
564:.
536:.
435:(
433:3
429:5
427:H
425:2
386:3
382:2
378:3
374:2
325:2
323:)
321:3
308:2
306:)
304:3
291:2
289:)
287:3
195:6
193:)
191:3
179:5
177:)
175:3
122:4
120:)
118:3
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