Phosphorylation and Amine-induced Dephosphorylation of 4-Chlorocoumarin-3-carboxaldehyde and 4-Chloro-3-(β, β-dicyanoethenylidene) coumarin

MD Khidre

Index: Khidre, Maha Darwish Phosphorus, Sulfur and Silicon and the Related Elements, 2003 , vol. 178, # 10 p. 2147 - 2158

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Abstract

4-Chlorocoumarin-3-carboxaldehyde (1) and 4-chloro-3-(g, g-dicyanoethenylidene) coumarin (2) produce their respective 1: 1 phosphonate adducts (5a-c) and (6a-c) upon reaction with the appropriate dialkylphosphonates (3a-c). Compounds 5 undergo dechlorination and dephosphorylation upon reaction with certain primary aliphatic amines to yield 9 (or 10) according to the nature of the amine used. Compounds 1 and 2 undergo ...