Ozonolysis of alkenes under traditional conditions generates peroxide intermediates that must be decomposed in a separate step in order to obtain the carbonyl product(s). However, ozonolysis in the presence of stoichiometric pyridine results in the direct formation of the carbonyl product(s), without generation of the peroxide byproducts and without consumption of pyridine. The reaction is postulated to involve the decomposition of carbonyl oxides via the pyridine-promoted conversion to a previously unobserved class of intermediates that fragment to release the carbonyl product and regenerate pyridine.

Pyridine as an organocatalyst for the reductive ozonolysis of alkenes

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.