Equilibrium between a cyclotrisilene and an isolable base adduct of a disilenyl silylene

Nature Chemistry

Volumn 5, Issue 10, 2013, Pages 876-879

  Cowley, Michael J ^a   Huch, Volker ^a   Rzepa, Henry S ^b   Scheschkewitz, David ^a,b  

^a SAARLAND UNIVERSITY   (Germany)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOTRISILENE; DISILENYL SILYLENE; ORGANOSILICON DERIVATIVE; SILICON; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; SILICON; VINYL COMPOUNDS;

EID: 84884846446     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1751     Document Type: Article

References (27)

1. Trinquier, G. & Malrieu, J. Nonclassical distortions at multiple bonds. J. Am. Chem. Soc. 109, 5303-5315 (1987)
2. Filtvedt,W. O., Holt, A., Ramachandran, P. A. & Melaaen,M. C. Chemical vapor deposition of silicon from silane: review of growth mechanisms and modeling/scaleup of fluidized bed reactors. Sol. Energ. Mat. Sol. Cells 107, 188-200 (2012)
3. Kira, M. & Iwamoto, T. Progress in the chemistry of stable disilenes. Adv. Organomet. Chem. 54, 73-148 (2006)
4. Mizuhata, Y., Sasamori, T. & Tokitoh, N. Stable heavier carbene analogues. Chem. Rev. 109, 3479-3511 (2009)
5. West, R. Inorganic chemistry: two-armed silicon. Nature 485 49-50 (2012)
6. Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W. W. & Bertrand, G. Cyclopropenylidenes: from interstellar space to an isolated derivative in the laboratory. Science 312, 722-724 (2006)
7. Hutton, R., Manion,M. & Roth, H. Geometric isomers of vinylmethylene. J. Am. Chem. Soc. 96, 4680-4682 (1974)
8. Weber, W. & de Meijere, A. Tetrachlorovinylcarbene from tetrachlorocyclopropene; facile synthesis of vinylcyclopropanes. Angew. Chem. Int. Ed. Engl. 19, 138-140 (1980)
9. Diver, S. T. Ruthenium vinyl carbene intermediates in enyne metathesis. Coord. Chem. Rev. 251, 671-701 (2007)
10. Moss, R. A. et al. Kinetic studies of the cyclization of singlet vinylchlorocarbenes. Org. Lett. 7, 4645-4648 (2005) (Pubitemid 41507062)
11. Kosa, M., Karni, M. & Apeloig, Y. Trisilaallene and the relative stability of Si3H4 isomers. J. Chem. Theory. Comput. 2, 956-964 (2006)
12. Asay, M., Jones, C. & Driess, M. N-Heterocyclic carbene analogues with lowvalent group 13 and group 14 elements: syntheses, structures, and reactivities of a new generation of multitalented ligands. Chem. Rev. 111, 354-96 (2011)
13. Yao, S., Xiong, Y. & Driess, M. Zwitterionic and donor-stabilized N-heterocyclic silylenes (NHSis) for metal-free activation of small molecules. Organometallics 30, 1748-1767 (2011)
14. Wang, Y. et al. A stable silicon(0) compound with a Si?Si double bond. Science 321, 1069-1071 (2008)
15. Ghadwal, R. S., Roesky, H. W., Merkel, S., Henn, J. & Stalke, D. Lewis base stabilized dichlorosilylene. Angew. Chem. Int. Ed. 48, 5683-5686 (2009)
16. Filippou, A. C., Chernov, O. & Schnakenburg, G. SiBr2(Idipp): a stable N-heterocyclic carbene adduct of dibromosilylene. Angew. Chem. Int. Ed. 48, 5687-5690 (2009)
17. Filippou, A. C., Chernov, O., Blom, B., Stumpf, K.W. & Schnakenburg, G. Stable N-heterocyclic carbene adducts of arylchlorosilylenes and their germanium homologues. Chem. Eur. J. 16, 2866-2872 (2010)
18. Baird, M. S. Thermally induced cyclopropene-carbene rearrangements: an overview. Chem. Rev. 103, 1271-1294 (2003)
19. Baird, M. S., Al Dulayymi, J. R., Rzepa, H. S. & Thoss, V. An unusual example of stereoelectronic control in the ring opening of 3,3-disubstituted 1,2-dichlorocyclopropenes. Chem. Commun. 1323-1325 (1992)
20. Shimoda, T. et al. Solution-processed silicon films and transistors. Nature 440, 783-786 (2006)
21. Bejan, I. & Scheschkewitz, D. Two Si-Si double bonds connected by a phenylene bridge. Angew. Chem. Int. Ed. 46, 5783-5786 (2007) (Pubitemid 47172212)
22. Abersfelder, K. & Scheschkewitz, D. Syntheses of trisila analogues of allyl chlorides and their transformations to chlorocyclotrisilanes, cyclotrisilanides, and a trisilaindane. J. Am. Chem. Soc. 130, 4114-4121 (2008) (Pubitemid 351429882)
23. Yamaguchi, T., Sekiguchi, A. & Driess, M. An N-heterocyclic carbene-disilyne complex and its reactivity toward ZnCl2. J. Am. Chem. Soc. 132, 14061-14063 (2010)
24. Leszczyńska, K. et al. Reversible base coordination to a disilene. Angew. Chem. Int. Ed. 51, 6785-6788 (2012)
25. Power, P. P. Main-group elements as transition metals. Nature 463, 171-177 (2010)
26. Fokin, A. et al. Stable alkanes containing very long carbon-carbon bonds. J. Am. Chem. Soc. 134, 13641-13650 (2012)
27. Kuhn, N. & Kratz, T. Synthesis of imidazol-2-ylidenes by reduction of imidazole-2 (3H)-thiones. Synthesis 561-561 (1993)