63777-67-3Relevant academic research and scientific papers
Aqueous micellar medium in organic synthesis: Alkylations and Michael reactions of benzotriazole
Mashraqui, Sabir Hussain,Kumar, Sukeerthi,Mudaliar, Chandrasekhar Dayal
, p. 2133 - 2138 (2001)
The feasibility of aqueous micelles of cetyltrimethylammonium bromide in catalyzing C-N bond formation has been studied with respect to N-alkylations of benzotriazole (Bt). Alkylations with various alkylating agents and the addition of Bt across activated double bonds in the Michael fashion occurred successfully in fair-to-good yields in the aqueous micellar regime. These reactions provided a mixture of N-1 and N-2 alkylated products, with a marked preference for N-1 over N-2 isomers. Micellar catalysis has been evaluated experimentally to indicate over a 50% micellar contribution to these alkylations in contrast to their aqueous counterparts. Since, N-alkyl benzotriazoles are of potential biological interest, the present micellar procedure offers a convenient alternative to other available methods.
Dimerizations of 2-alkylbenzotriazoles and chemical evidence of radical intermediates from X-ray studies
Katritzky, Alan R.,Jesorka, Aldo,Wang, Jin,Yang, Baozhen,Wu, Jing,Steel, Peter J.
, p. 745 - 755 (2007/10/03)
Treatment of 2-alkylbenzotriazoles with lithium diisopropylamide (LDA) at -78°C gave, depending on workup conditions, either dimers of the type Bt2CHR-CHRBt2 (2) (Bt2 = benzotriazol-2-yl), or mixtures of symmetrical Z and E olefins (3) (RCH=CHR), in high yields via radical intermediates. The racemic and meso isomers of 2, which differ substantially in properties such as melting points, 1H and 13C NMR, were isolated and characterized (three by X-ray crystallography). Both the meso and racemic dimers of 2 were reduced by Na to give mixtures of Z and E olefins in high yields with the elimination of the benzotriazole anion. 2-Alkylbenzotriazoles (1) were also converted by Na into the corresponding alkanes and benzotriazole. The intermediates were trapped by benzophenone to give, depending on the reaction procedure (see Scheme 2), adducts 6 or adducts 6 with dimers 2, benzotriazol-2-ylalkene 7 and compound 8 (R = H), compound 9 (R = CH3). Several compounds with dibenzotriazol-2-yl groups or benzotriazol-1-yl and benzotriazol-2-yl groups in the same molecule were synthesized and further investigated via lithiation followed by the addition of benzophenone or benzaldehyde. This further indicated that the radical reaction is faster than the nucleophilic reaction. VCH Verlagsgesellschaft mbH, 1996.
