Tetrahedron

Ortho-selective side-chain nitration of α-Bromoacylpolymethylbenzenes and its application to the syntheses of indan-1-one and inden-1-one derivatives

T Keumi, K Matsuura, N Nakayama, T Tsubota, T Morita…

Index: Keumi, Takashi; Matsuura, Kazunori; Nakayama, Norihiro; Tsubota, Toshiaki; Morita, Toshio; et al. Tetrahedron, 1993 , vol. 49, # 3 p. 537 - 556

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Citation Number: 11

Abstract

α-Bromoacylpolymethylbenzenes 2a-m react with fuming nitric acid in acetic anhydride to give 2-(nitromethyl)-(α-bromoacyl) polymethylbenzenes 3a-m in good isolated yields. Compounds 3a-j undergo the intramolecular nucleophilic substitution/cyclization in the presence of 1 equiv. of base either in benzene or N, N-dimethylformamide (DMF) to provide the corresponding substituted 3-nitroindan-1-ones 4a-j in quantitative yields as mixtures of ...