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Synlett 1991; 1991(7): 505-506
DOI: 10.1055/s-1991-20779
DOI: 10.1055/s-1991-20779
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tert-Butyl Vinyl Ethers from tert-Butoxymethyl Phenyl Sulfone
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Publication History
Publication Date:
07 March 2002 (online)
Two different reaction pathways are given from an alkyl halide to the homologous tert-butyl vinyl ether, both of them involving lithiated tert-butoxymethyl phenyl sulfone [tert-butoxy(phenylsulfonyl)methyllithium]. This new synthetic reagent is alkylated and the resulting sulfone is exposed to base-promoted elimination in the first route. The second route involves the coupling of this organometallic species with the lithium derivative of the phenyl alkyl sulfone (1-phenylsulfonylalkyllithium) corresponding to the halide, and provides a new example of reaction between two carbenoids, one of them acting as an electrophile.