Intramolecular Schmidt reactions of azides with carbocations: synthesis of bridged-bicyclic and fused-bicyclic tertiary amines

…, R Walavalkar, JM Schkeryantz, WK Fang…

Index: Pearson, William H.; Walavalkar, Rajesh; Schkeryantz, Jeffrey M.; Fang, Wen-Kui; Blickensdorf, James D. Journal of the American Chemical Society, 1993 , vol. 115, # 22 p. 10183 - 10194

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Citation Number: 91

Abstract

Abstract: Aliphatic azides were captured intramolecularly by carbocations, producing aminodiazonium ion intermediates. Carbon-to-nitrogen rearrangement then occurred, generating bridged-or fused-bicyclic a-amino carbocations or iminium ions, depending on the geometry about the C (+)-N bond. In the bridged systems, rapid elimination of the a- amino carbocations produced twisted enamines with 1-azabicyclo [3.2. 2] nonene, 1- ...