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.
G. Bartoli, R. Leardini, M. Lelli and G. Rosini, J. Chem. Soc., Perkin Trans. 1, 1977, 884 DOI: 10.1039/P19770000884
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