We introduced an efficient method for the synthesis of allenic sulfones and demonstrated the lithiation of certain substituted allenic sulfones in conjunction with their use as nucleophiles. As part of our continued interest in this chemistry, we initiated a study of the addition of lithiated, allenic sulfones to cyclobutenones. Our initial expectation was that we would achieve a synthesis of substituted phenols. However, in most instances, what we obtained was a valence tautomer of the expected phenol. This process is general and offers a unique opportunity of functionalization of the products to indeed afford phenols, but also a wide range of other products as well.

Nonaromatic valence tautomers of substituted phenols via a 6π electrocyclization

ACS Spring 2022

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