2001•Organic LettersRequires access

Synthesis and Reactivity of Silyl Vinylketenes: A Formal Interrupted Dötz Benzannulation with Unexpected Silyl Migration

William H. Moser, Liangdong Sun, John C. Huffman

Abstract

[reaction: see text]. An efficient method for the generation of silyl vinylketenes from the thermal reaction of Fischer carbene complexes with silyl-substituted phenylacetylenes is described. Although the silyl vinylketene products are highly stable, conditions have been identified to induce a benzannulation/silyl migration process, providing aromatic silyl ethers.

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Available abstract

Key concepts: Silylation, Chemistry, Carbene, Reactivity (psychology), Medicinal chemistry, Catalysis, Organic chemistry, Pathology