Reactions of O, O-diprotonated nitro olefins with benzenes. Formations of phenylacetones, 4H-1, 2-benzoxazines and biarylacetone oximes

T Ohwada, K Okabe, T Ohta, K Shudo

Index: Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi Tetrahedron, 1990 , vol. 46, # 21 p. 7539 - 7555

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Citation Number: 32

Abstract

O, O-diprotonated nitro olefins undergo three alternative electrophilic reactions which yield α- phenylacetones, 4H-1, 2-benzoxazines and biphenylacetone oximes depending on the reaction conditions (temperature and time) and aromatic substrates. Although these reactions are seemingly divergent, a common intermediate of a phenylated protonated aci- nitro species, derived from the dication, is postulated to be involved in the reactions. ...