94023-76-4Relevant academic research and scientific papers
Tandem Wolff rearrangement-'tert-amino effect' sequence: Synthesis of 2-oxoindolinium enolate derivatives
Leost, Francoise,Chantegrel, Bernard,Deshayes, Christian
, p. 7557 - 7576 (2007/10/03)
The thermolysis of 1-diazo-2-oxo-(2-N,N-disubstituted aminophenyl)ethylphosphonates 1 gave rise to 2-oxoindolinium enolate derivatives 4 through Wolff rearrangement and interaction of the tert-amino moiety with the ketene functionality. Variable amounts of either ammonium ylides 5 or of products resulting from their transformations were also formed during the course of the reaction. If the amino moiety was substituted by a benzyl or an allyl group, indolinones, resulting from [1,3] or [1,2] benzylic or allylic shifts, were isolated in place of compounds 4 and 5.
A New Reduction of Some Carboxylic Esters with Sodium Borohydride and Zinc Chloride in the Presence of a Tertiary Amine
Yamakawa, Tomio,Masaki, Mitsuo,Nohira, Hiroyuki
, p. 2730 - 2734 (2007/10/02)
In the presence of a tertiary amine, sodium borohydride (NaBH4) combined with zinc chloride (ZnCl2) showed powerful reducing properties and carboxylic esters were smoothly reduced to their corresponding alcohols which were not obtained by reduction with NaBH4 and ZnCl2 alone.Tetrahydrofuran (THF) was an efficient solvent, and the effective molar ratio of the reducing agents, NaBH4:ZnCl2:tertiary amine, was 2:1:1.In particular, aminobenzoates such as anthranilic esters, were reduced to aminobenzyl alcohols with high yields without the addition of a tertiary amine.Further, it was also found that this combination reduced nitro, cyano, and amido groups to their corresponding amino groups.
