Potential Protecting Group Strategy for Disila Analogues
of Vinyllithiums: Synthesis and Reactivity of a 2,4,6-Trimethoxyphenyl-Substituted
Disilene
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Abstract
Proof
of concept for the protection of the nucleophilic functionality of
disilenidesdisila analogues of vinyllithiumwith preservation
of the SiSi 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 Tip<sub>2</sub>SiSi(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 SiSi 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 Me<sub>3</sub>SiCl reveals KC<sub>8</sub> as a highly
appropriate reducing agent for the selective deprotection