Reactions of nitrobenzothiazoles with Grignard reagents. Orientation of alkylation with respect to the nitro-group position

Abstract
Nitrobenzothiazoles react with Grignard reagents giving alkyl-nitroso-compounds, except the 4-nitro-isomer which affords alkyl-nitro-derivatives. The observed highly regiospecific alkylation can be interpreted in terms of the stability of a cyclohexadiene-type intermediate. Detailed mass spectra of the products are reported.

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