2 research outputs found
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
disilenidesî—¸disila analogues of vinyllithiumî—¸with preservation
of the Siî—»Si bond is reported. 1-Iodo-2,4,6-trimethoxybenzene
(TMOP-I) reacts with lithium trisÂ(2,4,6-triisopropylphenyl)Âdisilenide
(<b>1</b>), affording the disilene Tip<sub>2</sub>Siî—»SiÂ(Tip)ÂTMOP
(<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 Siî—»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 Me<sub>3</sub>SiCl reveals KC<sub>8</sub> as a highly
appropriate reducing agent for the selective deprotection
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
disilenidesî—¸disila analogues of vinyllithiumî—¸with preservation
of the Siî—»Si bond is reported. 1-Iodo-2,4,6-trimethoxybenzene
(TMOP-I) reacts with lithium trisÂ(2,4,6-triisopropylphenyl)Âdisilenide
(<b>1</b>), affording the disilene Tip<sub>2</sub>Siî—»SiÂ(Tip)ÂTMOP
(<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 Siî—»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 Me<sub>3</sub>SiCl reveals KC<sub>8</sub> as a highly
appropriate reducing agent for the selective deprotection