Activation of nitriles by hydrogen bonding in cycloadditions with nitrile oxides

A Corsaro, U Chiacchio, P Caramella…

Index: Corsaro, Antonino; Chiacchio, Ugo; Caramella, Pierluigi; Purrello, Giovanni Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 949 - 952

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Citation Number: 13

Abstract

950 A. Corsaro, U. Chiacchio, Р. Caramella and G. Purrello Vol.21 [8] undergo preferential syn additions, which maximize hydrogen bonding effects. To test the hydrogen bonding hypothesis we have stud- ied the cycloadditions of benzonitrile oxide to the ortho- aminobenzonitriles 9a-e. These dipolarophiles seemed very convenient models to us. They retain the same geo- metrical features of the prevailing (Z) stereo isomer 6 of /3-aminocinnamonitriles, ie ...