Radical addition to carbenoids. Chain reactions of α-diazo carbonyl compounds with triorganotin hydrides, tris (trimethylsilyl) silane and allyltributylstannane

HS Dang, BP Roberts

文献索引：Dang, Hai-Shan; Roberts, Brian P. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 8 p. 769 - 775

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摘要

α-Diazo ketones RC (O) CHN2 react with tributyltin hydride at 60° C in benzene to give the corresponding α-stannyl ketones RC (O) CH2SnBu3, which exist in equilibrium with the stannyl enol ether tautomers R (Bu3SnO) CCH2. The reactions are initiated by di-tert-butyl hyponitrite and follow a freeradical chain mechanism. Triphenyltin hydride and tris (trimethylsilyl) silane [(TMS) 3SiH] react similarly, the latter to yield the α-silyl ketone RC (O ...