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Issue 3, 2012
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Chemistry of functionalized silylenes

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Recent years have witnessed important developments in organosilicon chemistry, courtesy to the high yield access of stable monomeric chlorosilylene (LSiCl, L = PhC(NtBu)2) and N-heterocyclic carbene (NHC) stabilized dichlorosilylene (L1SiCl2, L1 = 1,3-bis(2,6-iPr2C6H3)imidazol-2-ylidene) by dehydrochlorination technique using strong bases such as N-heterocyclic carbenes or LiN(SiMe3)2 as HCl scavenger. The chemistry of functionalized silylenes is markedly different from the previously reported dicoordinate silylenes. Their utility as synthons is well documented which paves the way for several striking compounds, e.g. monosilaoxiranes, CSi2P derivative, CSi3P cation, a dimer of silaisonitrile (Si2N2) with dicoordinate Si atoms etc. This study also unravels that these functionalized silylenes are proficient at activating phosphorus, and the functional group attached to the α-position of the silicon(II) centre plays a key role to determine the final product. The reaction of P4 with LSiCl affords a zwitterionic Si2P2 ring, while with LSiN(SiMe3)2 it gives an acyclic Si2P4 derivative. Another recent achievement in this field is the successful isolation of a valence isomer of disilyne known as the inter-connected bis-silylene. This perspective portrays the chemistry of functionalized silylenes which will attract great attention, heading for the further development of organosilicon chemistry.

Graphical abstract: Chemistry of functionalized silylenes

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Article information

04 Oct 2011
27 Oct 2011
First published
08 Nov 2011

Chem. Sci., 2012,3, 659-682
Article type

Chemistry of functionalized silylenes

S. S. Sen, S. Khan, P. P. Samuel and H. W. Roesky, Chem. Sci., 2012, 3, 659
DOI: 10.1039/C1SC00757B

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