Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene

• DOI: 10.1021/acs.orglett.0c01510
• Publication Date: 2020-05-21T17:45:20Z
• Authors: Matthew S. McVeigh; Andrew V. Kelleghan; Michael M. Yamano; Rachel R. Knapp; Neil K. Garg
• Keywords: Trifluoromethanesulfonate

Transient strained cyclic intermediates have become valuable in modern synthetic chemistry. Although silyl triflate precursors to are most often employed, the instability of some triflates warrants development alternative precursors. We report syntheses tosylate cyclohexyne, 1,2-cyclohexadiene, and 1,2-cycloheptadiene. The resultant undergo trapping situ give cycloaddition products. Additionally, results competition experiments between tosylates reported.