Intramolecular insertion of the isonitrile group into an oxygen–silicon bond. Synthesis of a 2-trimethylsilyloxazole via the α-isocyano silyl enol ether

…, T Dall'Occo, G Fantin, M Fogagnolo…

Index: Dondoni, Alessandro; Dall'Occo, Tiziano; Fantin, Giancarlo; Fogagnolo, Marco; Medici, Alessandro; Pedrini, Paola Journal of the Chemical Society, Chemical Communications, 1984 , # 4 p. 258 - 260

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Citation Number: 7

Abstract

Treatment of lithiated 4-methyloxazole (1b) with trimetylsilyl chloride gives the α-isocyano silyl enol ether (4b) which when heated in the presence of potassium hydroxide undergoes ring closure to the 2-trimethylsilyloxazole (5b) whose reactions with C-and S-electrophiles afford 2-substituted oxazoles.