Hindered ester formation by SN 2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides—novel application of HERON rearrangements

SA Glover, G Mo

文献索引：Glover, Stephen A.; Mo, Guoning Journal of the Chemical Society. Perkin Transactions 2, 2002 , # 10 p. 1728 - 1739

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被引用次数: 35

摘要

Treatment of N-acetoxy-N-alkoxyamides or N-alkoxy-N-chloroamides with sodium azide in aqueous acetonitrile results in SN2 displacement of chloride and the formation of reactive N- alkoxy-N-azidoamides. The reaction with N-acetoxy-N-benzyloxybenzamide has been studied kinetically (k294= 2 L mol− 1 s− 1) and azi