A general procedure has been set up to prepare, selectively, the N-monoalkylanilines, reacting (Z)-(tert-butylsulfanyl)(aryl)diazenes with alkyllithium (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, and then at room temperature. In optimal conditions the yields of the pure products (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.

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

BARBERO, Margherita;DEGANI, Jacopo;DUGHERA, Stefano;FOCHI, Rita
2003

Abstract

A general procedure has been set up to prepare, selectively, the N-monoalkylanilines, reacting (Z)-(tert-butylsulfanyl)(aryl)diazenes with alkyllithium (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, and then at room temperature. In optimal conditions the yields of the pure products (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.
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742
750
N-alkylanilines; amines; diazonium compounds; di­azosulfides; allkyllithium
BARBERO M; DEGANI I; S. DUGHERA; FOCHI R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1127
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