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Unusual reactivity of lithiated 2‐alkylbenzotriazoles
Author(s) -
Katritzky Alan R.,
Wu Jing,
Kuzmierkiewicz Wojciech,
Rachwal Stanislaw,
Balasubramanian Marudai,
Steel Peter J.
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940103
Subject(s) - chemistry , benzophenone , benzaldehyde , adduct , reactivity (psychology) , alkyl , alkylation , halide , molecule , carbon atom , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.