Coumalyl chloride

Coumalyl chloride (330) reacts normally with ethyleneimine to give the carboxamide (333), but primary and other secondary amines such as benzylamine, r-butylamine, diethyl-amine and pyrrolidine give unsaturated anhydrides (332), possibly through an acyclic intermediate (331). Aniline gives a mixture of both kinds of product (78JOC4415). 

Coumalyl chloride reactions, 3, 691 Coumaphos against ectoparasites veterinary use, 1, 217 Coumaranone H NMR, 4, 579 synthesis, 3, 849-850 Coumaran-2-ones, 4, 579 IR spectra, 4, 590 reactions, 4, 649 structure, 4, 552 synthesis, 4, 128... 

The procedure for preparing methyl coumalate is based on a method described by von Pechmann. Methyl coumalate has also been prepared by direct esterification of the reaction mixture from malic acid and fuming sulfuric acid and from coumalyl chloride and methanol. ... 

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