Potential Protecting Group Strategy for Disila Analogues of Vinyllithiums: Synthesis and Reactivity of a 2,4,6-Trimethoxyphenyl-Substituted Disilene

Abstract

Proof of concept for the protection of the nucleophilic functionality of disilenidesdisila analogues of vinyllithiumwith preservation of the SiSi bond is reported. 1-Iodo-2,4,6-trimethoxybenzene (TMOP-I) reacts with lithium tris­(2,4,6-triisopropylphenyl)­disilenide (<b>1</b>), affording the disilene Tip₂SiSi­(Tip)­TMOP (<b>2</b>) in high yield. The presence of the TMOP group in disilene <b>2</b> enables the regioselective addition of polar substrates to the SiSi double bond, including water, ammonia, acetylenes, and isocyanides. NMR spectroscopic analysis of the reductive cleavage of the TMOP group and subsequent trapping of the corresponding disilenides with Me₃SiCl reveals KC₈ as a highly appropriate reducing agent for the selective deprotection