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Étude comparative de la décarboxylation des acides (benzothiazolyl‐2)‐acétique, ‐3‐propionique, ‐glyoxylique et ‐pyruvique
Author(s) -
Baudet Pierre,
Otten Claude
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530715
Subject(s) - chemistry , zwitterion , decarboxylation , acetic acid , carboxylation , glyoxylic acid , hydrochloride , medicinal chemistry , pyruvic acid , salt (chemistry) , organic chemistry , catalysis , molecule
Benzothiazol‐2‐yl glyoxylic acid and α‐amino‐benzothiazol‐2‐yl acetic acid hydrochloride undergo decarboxylation at room temperature. This facile decarboxylation seems to depend on the following requirements: (a) the formation of a planar zwitterion; (b) a distance of about 2.2 Å between the charges of the zwitterion; (c) the stabilisation of the intermediate carbanion. In fact the following compounds which do not fulfil these three conditions do not decarboxylate at room temperature: α‐hydroximino benzothiazol‐2‐yl acetic acid, α‐amino benzothiazol‐2‐yl acetic acid as internal salt, benzothiazol‐2‐yl acetic acid, 3‐(benzothiazol‐2‐yl)‐propionic acid and benzothiazol‐2‐yl pyruvic acid.