Photodisulfidation of alkenes with linear disulfides: Reaction scope and kinetics

Thiol-ene and thiol-yne photomediated conjugations have received substantial attention in research practice. Herein is presented the photodisulfidation of alkenes based on radical-mediated 1:1 reaction a disulfide vinyl ether, which provides an additional route for formation types sulfides seen thiol-ene polymers. Although similar linkages are formed, this approach starting with disulfides expected to benefits over reactions including extended shelf life compared thiols, reduced shrinkage stress, increased refractive index resulting materials. It was determined that ethers were only capable undergoing under ambient conditions reasonable timescales. The between performed well variety solvents providing modest excellent yields (100% bis(1-methylacetate) (DSMA)/triethyleneglycol divinylether (TEGDVE)) numerous substrates evaluated. mechanism involves auto-propagating cycle thiyl radicals add into either end ether form thio-ether thio-acetal final product. Finally, although rate slower than reaction, proceeds relatively rapidly explored conditions.