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Paper | Regular issue | Vol 71, No. 1, 2007, pp.27-38
Published online, 24th November, 2006
DOI: 10.3987/COM-06-10882
Regioselectivity in the 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides and Organic Azides with Bromocarbazole-1,4-diones

Muriel Compain-Batissou, Jacques Gentili, Nadia Walchshofer, Monique Domard, Bernard Fenet, and Zouhair Bouaziz*

*ISPB, EZ3741, University of Claude Bernard Lyon 1, 8 Avenue Rockefeller, 69373 Lyon cedex 08, France

Abstract

The effect exerted by the presence of a bromine atom in 2 or 3 position of a carbazole-1,4-dione on the regiocontrol of 1,3-dipolar cycloaddition reactions with nitrile oxides and organic azides was investigated. Comparison with the results obtained with 2,3-unsubstituted-carbazole-1,4-dione shows that bromine substituents on para-carbazolequinones effectively orient the 1,3-dipolar cycloadditions. The regiochemistry observed may be explained by the orienting effect of the bromine atom independently of the values of the orbital coefficients.