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High Yield Access to Silylene RSiCl (R = PhC(NtBu)2) and Its Reactivity toward Alkyne: Synthesis of Stable Disilacyclobutene

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posted on 27.01.2010, 00:00 authored by Sakya S. Sen, Herbert W. Roesky, Daniel Stern, Julian Henn, Dietmar Stalke
Two new approaches for synthesizing RSiCl, (R = PhC(NtBu)2) are reported by the reaction of RSiHCl2 with bis-trimethyl silyl lithium amide and N-heterocyclic carbene respectively. In the former method silylene is produced in 90% yield. The silylene was treated with biphenyl alkyne to afford the disilacyclobutene system. This is a rare example of two five-coordinate silicon centers arranged adjacent to each other in a four-membered ring. Furthermore, we fluorinated the four-membered ring by trimethyltin fluoride to obtain the fluoro substituted disilacyclobutene.

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