Reaction of silyldihalomethyllithiums with nitriles: Formation of α-keto acylsilanes via azirines and 1,3-rearrangement of silyl group from C to N
A synthesis of α-keto acylsilanes, where 2-bromo-2H-azirine participates as a key intermediate, is reported. The reaction of silyldibromomethyllithium with aryl nitriles provides α-keto acylsilanes in good yields. Interestingly, silyldichloromethyllithium induces aza-1,3-Brook rearrangement of the silyl group in th reaction with nitriles. The rearrangement enables a three-component coupling reaction in a one-pot operation. Copyright
A New, General Route to γ,δ-Unsaturated α,α-Dichloroketones from Allyl 2,2,2-Trichloroethyl Ethers via the Sigmatropic Rearrangement of Intermediary 2,2-Dichlorovinyl Ethers
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Morimoto, Toshiaki,Sekiya, Minoru
p. 308 - 310
(2007/10/02)
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