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

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 (1), affording the disilene Tip(2)Si=Si(Tip)TMOP (2) in high yield. The presence of the TMOP group in disilene 2 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.