Organic letters

Base-promoted reactions of dichlorocarbene adducts of cyclic enamines: A new route to annulated pyrroles

AC Bissember, AT Phillis, MG Banwell, AC Willis

Index: Bissember, Alex C.; Phillis, Andrew T.; Banwell, Martin G.; Willis, Anthony C. Organic Letters, 2007 , vol. 9, # 26 p. 5421 - 5424

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Citation Number: 11

Abstract

The adducts 1−10 used in the present study were generally prepared (29−85%) by subjecting the relevant enamine to reaction with chloroform or bromoform and sodium hydroxide in the presence of the phase-transfer catalyst triethylbenzylammonium chloride (TEBAC) under conditions first defined by Ma̧kosza. 5 Despite the propensity of gem-dihalogenocyclopropanes carrying electron-donating substituents to undergo facile electrocyclic ring cleavage, 6 these ...