Tetrahedron

AlCl 3–NaI (NaBr)–t-BuOH: mild, chemo-and stereoselective reagents for hydrohalogenation of propiolic derivatives

L Feray, P Perfetti, M Bertrand

Index: Feray, Laurence; Perfetti, Patricia; Bertrand, Michele Tetrahedron, 2009 , vol. 65, # 42 p. 8733 - 8737

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Citation Number: 3

Abstract

(Z)-β-Iodo-propenamides and-β-iodo-propenoic esters were selectively prepared in high yields, at room temperature, through reaction of 2-propynamides and 2-propynoic esters, respectively, with AlCl3 and NaI in the presence of t-BuOH in dichloromethane. These experimental conditions are compatible with the presence of acid sensitive acetal groups. Alternative use of EtOH or H2O in place of t-BuOH was investigated.(Z)-Bromo- ...