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Carbanions derived from 2-alkylthiobenzothiazoles. A novel α-lithiomethyl mercaptan synthon for mercaptomethylation
Journal article   Peer reviewed

Carbanions derived from 2-alkylthiobenzothiazoles. A novel α-lithiomethyl mercaptan synthon for mercaptomethylation

Alan R Katritzky, Jose M Aurrecoechea and Luis M. Vazquez de Miguel
Journal of the Chemical Society, Perkin Transactions 1, (4), pp.769-774
1987

Abstract

2-Methylthiobenzothiazole readily gives a methyl group lithio derivative which reacts cleanly with electrophiles. The products are conveniently converted into the corresponding thiols by BuLi at -78 °C, and this sequence thus provides a convenient two-step mercaptomethylation procedure for alkyl halides, aldehydes, and ketones.

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