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Synthesis 2003(5): 0742-0750
DOI: 10.1055/s-2003-38082
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A General Procedure to Selectively Prepare N-Alkylanilines by an Unexpected Reaction of (Z)-(tert-Butylsulfanyl)(aryl)diazenes with Alkyllithium Reagents

Margherita Barbero, Iacopo Degani*, Stefano Dughera*, Rita Fochi
Dip.to di Chimica Generale ed Organica Applicata, Università, C.so M. D"Azeglio 48, 10125 Torino, Italy
e-Mail: iacopo.degani@unito.it;
Further Information

Publication History

Received 18 December 2002
Publication Date:
21 March 2003 (online)

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Abstract

A general procedure has been set up to prepare, selectively, the N-monoalkylanilines 7, reacting (Z)-(tert-butylsulfanyl)(aryl)diazenes 3 with alkyllithium 6 (MeLi, BuLi, s-BuLi, n-C6H13Li). The reactions were carried out in anhydrous diethyl ether at 0 °C or -78 °C, depending on the reagent 6, and then at room temperature. In optimal conditions the yields of the pure products 7 (uncontaminated by dialkylation products) were from good to excellent: for 38 considered examples, 34 were positive with yields varying between 61% and 91% (average yield 78%). Collateral proofs were carried out to support a hypothesized reaction mechanism.

Key words

N-alkylanilines - amines - diazonium compounds - di­azosulfides - allkyllithium

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