Issue 9, 2002

Intramolecular nucleophilic catalysis and the exceptional reactivity of N-benzyloxycarbonyl α-aminophosphonochloridates

Abstract

The chloridate BnOCONHCH2P(O)(OMe)Cl is 103–104 times more reactive than ClCH2P(O)(OMe)Cl in substitution with PriOH; the α,α-dimethyl analogue is no less reactive and the N-methyl derivative is more reactive; nucleophilic participation (catalysis) by the carbamate group is implicated.

Graphical abstract: Intramolecular nucleophilic catalysis and the exceptional reactivity of N-benzyloxycarbonyl α-aminophosphonochloridates

Article information

Article type
Paper
Submitted
22 May 2002
Accepted
02 Jul 2002
First published
29 Jul 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1538-1543

Intramolecular nucleophilic catalysis and the exceptional reactivity of N-benzyloxycarbonyl α-aminophosphonochloridates

P. M. Cullis and M. J. P. Harger, J. Chem. Soc., Perkin Trans. 2, 2002, 1538 DOI: 10.1039/B204935J

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