Acidity of benzoylcarbamates in dimethyl sulfoxide. Confirmation of mixed N/O alkylation in the Mitsunobu reaction
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 655-658
- https://doi.org/10.1039/p29930000655
Abstract
Seventeen benzoyl-, 4-methoxybenzoyl- and 4-nitrobenzoyl-carbamates have been synthesized via their corresponding isocyanates and their acidities determined in dimethyl sulfoxide solution. Their pKa values span an interval of nearly 5 pK units (10.4–15.2). Selected derivatives have been investigated as amine synthons in the Mitsunobu reaction. In all cases mixtures of N- and O- alkylated products are obtained.Keywords
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