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Unusual reactivity of lithiated 2-alkylbenzotriazoles

✍ Scribed by Katritzky, Alan R. ;Wu, Jing ;Kuzmierkiewicz, Wojciech ;Rachwal, Stanislaw ;Balasubramanian, Marudai ;Steel, Peter J.

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
537 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Treatment of a 2‐alkylbenzotriazole (BtCH~2~R) (2) with LDA at −78°C produces rapidly a mixture of a coupling product (BtCHR–CHRBt) (5) and a compound formed from four molecules of the starting material (BtCHR–CHR–CHR–CHRBt) (6). A mixture of 2‐methylbenzotriazole and benzophenone, treated with LDA, gives adduct Ph~2~C(OH)CH~2~Bt (14) quantitatively whereas benzaldehyde does not react under these conditions. 2‐Alkylbenzotriazoles (2) are alkylated at the α‐carbon atom when their mixtures with alkyl halides are treated with LDA. magnified image

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