200:
609:
37:
24:
302:
573:
589:
906:
Denk, Michael; Lennon, Robert; Hayashi, Randy; West, Robert; Belyakov, Alexander V.; Verne, Hans P.; Haaland, Arne; Wagner, Matthias; Metzler, Nils (1994). "Synthesis and
Structure of a Stable Silylene".
315:
710:
239:
427:
of 1,1-dihalosilane. It has long been assumed that the conversion of metallic Si to tetravalent silicon compounds proceeds via silylene intermediates:
722:
357:. Silylene is a stable molecule as a gas but rapidly reacts in a bimolecular manner when condensed. Unlike carbenes, which can exist in the
1014:
703:
IUPAC Chemical
Nomenclature and Structure Representation Division (2013). "P-71.2.2.1". In Favre, Henri A.; Powell, Warren H. (eds.).
214:
580:
The α-amido centers stabilize silylenes by π-donation. The dehalogenation of diorganosilicon dihalides is a widely exploited.
855:
178:
371:
are formal derivatives of silylene with its hydrogens replaced by other substituents. Most examples feature amido (NR
714:
636:
322:
776:
Nagendran, Selvarajan; Roesky, Herbert W. (2008). "The
Chemistry of Aluminum(I), Silicon(II), and Germanium(II)".
661:
547:
934:
Driess, Matthias; Yao, Shenglai; Brym, Markus; Van Wüllen, Christoph; Lentz, Dieter (2006). "A New Type of
1019:
468:
608:
376:
59:
49:
738:
Mizuhata, Yoshiyuki; Sasamori, Takahiro; Tokitoh, Norihiro (2009). "Stable
Heavier Carbene Analogues".
615:
In this reaction diphenylsilylene is extruded from the trisila ring. The silylene can be observed with
499:
The formation of dimethylsilylene was demonstrated by conducting the dechlorination in the presence of
592:
350:
195:
87:
620:
408:
990:
955:
851:
820:
755:
718:
412:
338:
467:
Early observations of silylenes involved generation of dimethylsilylene by dechlorination of
141:
121:
982:
947:
916:
888:
843:
812:
785:
747:
600:
259:
97:
704:
656:
616:
566:
500:
461:
199:
457:
380:
293:
1008:
632:
504:
362:
588:
166:
682:
706:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
624:
392:
803:
Haaf, Michael; Schmedake, Thomas A.; West, Robert (2000). "Stable
Silylenes".
396:
278:
132:
36:
847:
565:-butyl-1,3-diaza-2-silacyclopent-4-en-2-ylidene, first described in 1994 by
416:
358:
994:
959:
824:
759:
628:
920:
892:
842:. The Chemistry of Functional Groups. Vol. 2. pp. 2463–2568.
669:
404:
400:
354:
346:
153:
986:
951:
816:
789:
751:
420:
572:
292:
Except where otherwise noted, data are given for materials in their
23:
973:
Moiseev, Andrey G.; Leigh, William J. (2006). "Diphenylsilylene".
587:
571:
424:
120:
110:
183:
365:
state, silylene (and all of its derivatives) are singlets.
871:
Skell, P. S.; Goldstein, E. J. (1964). "Dimethylsilene: CH
375:) or alkyl/aryl groups. Silylenes have been proposed as
310:
938:-Heterocyclic Silylene with Ambivalent Reactivity".
165:
96:
599:In one study diphenylsilylene is generated by
838:Gaspar, Peter; West, R. (1998). "Silylenes".
8:
840:The Chemistry of Organic Silicon Compounds
198:
140:
15:
619:at 520 nm and is short-lived with a
975:Journal of the American Chemical Society
940:Journal of the American Chemical Society
909:Journal of the American Chemical Society
881:Journal of the American Chemical Society
695:
391:Silylenes are generally synthesized by
244:
219:
194:
647:which is close to diffusion control.
226:Key: XMIJDTGORVPYLW-UHFFFAOYSA-N
7:
771:
769:
456:Similar considerations apply to the
507:product being pentamethyldisilane:
156:
576:Synthesis of an isolable silylene.
14:
607:
300:
265:
35:
29:Simplest silylene has R=Hydrogen
22:
296:(at 25 °C , 100 kPa).
271:
1:
805:Accounts of Chemical Research
595:is an example of a silylene.
546:A room-temperature isolable
1015:Inorganic silicon compounds
1036:
637:second order rate constant
290:
252:
235:
210:
80:
70:
58:
48:
43:
34:
21:
387:Synthesis and properties
848:10.1002/0470857250.ch43
685:, protonated silylenes
665:-heterocyclic silylene
596:
577:
551:-heterocyclic silylene
469:dimethyldichlorosilane
377:reactive intermediates
73:Hydrogen silicide(−II)
591:
575:
60:Systematic IUPAC name
593:Decamethylsilicocene
415:or abstraction), by
341:with the formula SiH
981:(45): 14442–14443.
921:10.1021/ja00085a088
893:10.1021/ja01061a040
286: g·mol
18:
621:chemical half-life
597:
578:
464:and bulk silicon.
460:, the reaction of
323:Infobox references
223:InChI=1S/H2Si/h1H2
16:
987:10.1021/ja0653223
952:10.1021/ja062928i
946:(30): 9628–9629.
817:10.1021/ar950192g
790:10.1021/om7007869
752:10.1021/cr900093s
724:978-0-85404-182-4
584:Related reactions
339:chemical compound
331:Chemical compound
329:
328:
179:CompTox Dashboard
122:Interactive image
17:generic silylene
1027:
999:
998:
970:
964:
963:
931:
925:
924:
915:(6): 2691–2692.
903:
897:
896:
887:(7): 1442–1443.
868:
862:
861:
835:
829:
828:
800:
794:
793:
773:
764:
763:
746:(8): 3479–3511.
740:Chemical Reviews
735:
729:
728:
700:
646:
644:
611:
603:of a trisilane:
601:flash photolysis
407:atom reactions (
313:
307:
304:
303:
285:
273:
267:
260:Chemical formula
203:
202:
187:
185:
169:
158:
144:
124:
100:
39:
26:
19:
1035:
1034:
1030:
1029:
1028:
1026:
1025:
1024:
1005:
1004:
1003:
1002:
972:
971:
967:
933:
932:
928:
905:
904:
900:
878:
874:
870:
869:
865:
858:
837:
836:
832:
811:(10): 704–714.
802:
801:
797:
778:Organometallics
775:
774:
767:
737:
736:
732:
725:
702:
701:
697:
692:
679:
675:
657:Carbene analogs
653:
642:
640:
617:UV spectroscopy
586:
567:Michael K. Denk
542:
538:
534:
530:
526:
522:
518:
514:
501:trimethylsilane
494:
490:
486:
482:
478:
462:methyl chloride
452:
448:
444:
438:
434:
389:
381:carbene analogs
374:
353:, the simplest
344:
332:
325:
320:
319:
318: ?)
309:
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283:
270:
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127:
114:
103:
90:
76:
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54:
30:
27:
12:
11:
5:
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1031:
1023:
1022:
1017:
1007:
1006:
1001:
1000:
965:
926:
898:
876:
872:
863:
856:
830:
795:
784:(4): 457–492.
765:
730:
723:
694:
693:
691:
688:
687:
686:
680:
677:
673:
667:
659:
652:
649:
613:
612:
585:
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543:
540:
536:
532:
528:
524:
520:
516:
512:
497:
496:
492:
488:
484:
480:
476:
458:direct process
454:
453:
450:
446:
442:
439:
436:
432:
388:
385:
372:
342:
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326:
321:
299:
298:
294:standard state
291:
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281:
275:
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268:
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196:DTXSID70884652
191:
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137:
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117:
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56:
55:
52:
46:
45:
41:
40:
32:
31:
28:
13:
10:
9:
6:
4:
3:
2:
1032:
1021:
1020:Free radicals
1018:
1016:
1013:
1012:
1010:
996:
992:
988:
984:
980:
976:
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966:
961:
957:
953:
949:
945:
941:
937:
930:
927:
922:
918:
914:
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902:
899:
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886:
882:
867:
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849:
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841:
834:
831:
826:
822:
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814:
810:
806:
799:
796:
791:
787:
783:
779:
772:
770:
766:
761:
757:
753:
749:
745:
741:
734:
731:
726:
720:
716:
712:
708:
707:
699:
696:
689:
684:
683:Silylium ions
681:
671:
668:
666:
664:
660:
658:
655:
654:
650:
648:
645:10 mol s
638:
634:
633:chemical trap
630:
626:
622:
618:
610:
606:
605:
604:
602:
594:
590:
583:
581:
574:
570:
568:
564:
560:
556:
552:
550:
510:
509:
508:
506:
502:
487:+ 2 K → Si(CH
474:
473:
472:
470:
465:
463:
459:
440:
430:
429:
428:
426:
422:
418:
414:
410:
406:
402:
398:
394:
386:
384:
382:
378:
370:
366:
364:
360:
356:
352:
348:
345:. It is the
340:
336:
324:
317:
312:
295:
289:
282:
280:
277:
276:
264:
261:
257:
256:
251:
245:
241:
234:
220:
216:
209:
201:
197:
193:
192:
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176:
175:
168:
164:
163:
161:
155:
151:
150:
143:
139:
138:
136:
134:
131:
130:
123:
119:
118:
116:
112:
107:
106:
99:
95:
94:
92:
89:
85:
84:
79:
69:
61:
57:
51:
47:
42:
38:
33:
25:
20:
978:
974:
968:
943:
939:
935:
929:
912:
908:
901:
884:
880:
866:
839:
833:
808:
804:
798:
781:
777:
743:
739:
733:
705:
698:
662:
625:microseconds
614:
598:
579:
562:
558:
554:
548:
545:
498:
466:
455:
390:
368:
367:
334:
333:
81:Identifiers
71:Other names
535:Si(H)−Si(CH
401:polysilanes
393:thermolysis
379:. They are
253:Properties
1009:Categories
857:0471967572
690:References
631:acts as a
397:photolysis
349:analog of
279:Molar mass
133:ChemSpider
109:3D model (
98:13825-90-6
88:CAS Number
64:Silylidene
50:IUPAC name
425:reduction
417:pyrolysis
409:insertion
369:Silylenes
351:methylene
995:17090011
960:16866506
825:11041835
760:19630390
651:See also
629:methanol
627:. Added
519:+ HSi(CH
423:, or by
413:addition
335:Silylene
75:Silicene
53:Silylene
670:Silenes
635:with a
623:of two
569:et al.
505:trapped
495:+ 2 KCl
431:Si + Cl
421:silanes
405:silicon
363:triplet
359:singlet
355:carbene
347:silicon
316:what is
314: (
167:6327230
154:PubChem
142:4885758
993:
958:
854:
823:
758:
721:
676:Si=SiR
503:, the
449:→ SiCl
435:→ SiCl
311:verify
308:
284:30.101
240:SMILES
44:Names
711:IUPAC
561:′-di-
527:→ (CH
511:Si(CH
403:, by
337:is a
215:InChI
111:JSmol
991:PMID
956:PMID
875:SiCH
852:ISBN
821:PMID
756:PMID
719:ISBN
563:tert
475:SiCl
445:+ Cl
441:SiCl
983:doi
979:128
948:doi
944:128
917:doi
913:116
889:doi
879:".
844:doi
813:doi
786:doi
748:doi
744:109
715:RSC
672:, R
641:1.3
639:of
553:is
479:(CH
419:of
399:of
395:or
361:or
184:EPA
157:CID
1011::
989:.
977:.
954:.
942:.
911:.
885:86
883:.
850:.
819:.
809:33
807:.
782:27
780:.
768:^
754:.
742:.
717:.
709:.
471::
411:,
383:.
272:Si
997:.
985::
962:.
950::
936:N
923:.
919::
895:.
891::
877:3
873:3
860:.
846::
827:.
815::
792:.
788::
762:.
750::
727:.
713:–
678:2
674:2
663:N
643:×
559:N
557:,
555:N
549:N
541:3
539:)
537:3
533:2
531:)
529:3
525:3
523:)
521:3
517:2
515:)
513:3
493:2
491:)
489:3
485:2
483:)
481:3
477:2
451:4
447:2
443:2
437:2
433:2
373:2
343:2
306:Y
269:2
266:H
186:)
182:(
113:)
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