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 Tip2Si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.