Isotopic Exchange in Olefin Ion–Molecule Reactions

Abstract

Isotopic exchange was examined in the products of ion–molecule reactions involving deuterated and undeuterated olefins. The results were used to obtain information regarding the structure of reaction intermediates, and the factors governing H–D exchange. Analysis of product distributions in mixtures of 2‐C₄D₈ with various pentenes and hexenes suggested quite specific structures for the reaction intermediates which were in good agreement with earlier work on undeuterated systems. In addition it was found that different products, which almost certainly arose from the same intermediate, showed significantly different degrees of H–D exchange.