Helvetica chimica acta

Zum Mechanismus der α??Alkinon??Cyclisierung: Synthese und Thermolyse von 1??(1??Methylcyclopentyl)[3??13C] prop??2??inon

M Koller, M Karpf, AS Dreiding

Index: Koller, Manuel; Karpf, Martin; Dreiding, Andre S. Helvetica Chimica Acta, 1983 , vol. 66, # 8 p. 2760 - 2768

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Citation Number: 13

Abstract

Summary The relative migratory aptitude of two acetylenic substituents in the a-alkynone cyclization, a thermal conversion of a-acetylenic ketones A to 2-cyclopentenones C, was investigated by isotope-labeling experiments. The a-alkynone [p-'3C]-1, specifically labeled with I3C at the P-acetylenic C-atom C (3), was synthesized by an intramolecular Wittig reaction (230-300') of the diacylmethylidenephosphorane ['3C]-7. The latter resulted from ...