Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization

…, LS Longo, J Zukerman-Schpector

Index: Ferraz, Helena M. C.; Longo Jr., Luiz S.; Zukerman-Schpector, Julio Journal of Organic Chemistry, 2002 , vol. 67, # 10 p. 3518 - 3521

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Citation Number: 21

Abstract

The reaction of a series of six-membered ring 3-alkenols with thallium trinitrate (TTN) in three different experimental conditions was studied. Either cyclization products or ring contraction products were obtained, depending on the structure of the substrate as well as the nature of the solvent. The reaction of a seven-membered ring 3-alkenol with TTN led to the ring contraction product exclusively.