Organic & biomolecular chemistry

Silicon and tin-directed Tiffeneau–Demjanov reaction

L Chow, M McClure, J White

Index: Chow, Leonie; McClure, Melanie; White, Jonathan Organic and Biomolecular Chemistry, 2004 , vol. 2, # 5 p. 648 - 650

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Citation Number: 14

Abstract

Silicon and tin substituents surprisingly have only a moderate directing effect on the Tiffeneau–Demjanov reaction. The low selectivity is rationalised as being due to the reactive nature of the diazonium ion leaving group, the weaker oxydiazene leaving group was found to give better yields of the silicon-directed ring expanded product.

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