Tetrahedron

Deoxygenation of isocyanates to isonitriles: A mechanistic study by nuclear magnetic resonance

JE Baldwin, AE Derome, PD Riordan

Index: Baldwin, Jack E.; Derome, Andrew E.; Riordan, Peter D. Tetrahedron, 1983 , vol. 39, # 18 p. 2989 - 2994

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Citation Number: 19

Abstract

Carbon-13 NMR has been used to show that the deoxygenation of isocyanates to isonitriles with t-butyldiphenylsilyl lithium proceeds via the intermediates (7 and 8). The silyl carboxamide (1) can be isolated but is thermally unstable rearranging to a mixture of silyl formamides (2). The spectroscopic properties of the silyl carboxamide (1) were found to be substantially different from those previously claimed for such compounds.