Reaction of pyridines with tetrachlorocyclopropene. A new synthesis of indolizines

…, KC Waterman, A Streitwieser Jr

Index: Smith; Waterman; Streitwieser Jr. Journal of Organic Chemistry, 1985 , vol. 50, # 18 p. 3360 - 3365

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Citation Number: 6

Abstract

Pyridines react with tetrachlorocyclopropene, TCCP, to give indolizine products in high yields. A mechanism is suggested in which successive nucleophilic reactions by the pyridine nitrogen lead to a cyclopropyl anion that undergoes electrocyclic ring-opening to the