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Mécanisme de l'hydrolyse acide des carbamates
Author(s) -
Hudson R. F.,
Searle R. J. G.,
Mancuso A.
Publication year - 1967
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.19670500402
Subject(s) - chemistry , carbonium ion , hydrolysis , halide , medicinal chemistry , alkyl , solvolysis , ion , olefin fiber , stereochemistry , organic chemistry , catalysis
N, N‐dialkyl carbamates decompose in strongly acidic media to carbon dioxide, olefin, alkyl halide and alcohol, the rate of reaction of the secondary esters closely following the acidity function. This fact, together with the variation in rate of hydrolysis of carbamates of cyclic alcohols with the ring size, shows that, unlike the solvolyses of the corresponding chloroformates which lead to carboxonium ions ( \documentclass{article}\pagestyle{empty}\begin{document}$ {\rm R - O -}\mathop {\rm C}\limits^{{\rm (+)}} = {\rm O} $\end{document} ), these reactions involve the intermediate formation of carbonium ions.