109384-93-2Relevant articles and documents
Photochemical or Thermochemical in Situ Generation of Vinyl Ketenes and their Cycloadditions
Naidorf-Meir, S.N.,Hassner, A.
, p. 2429 - 2438 (2007/10/02)
Photolysis of cyclobutenone 1 at room temperature constitutes a mild method of in situ generation of vinyl ketene 2 which can be trapped with O or N nucleophiles as well as with olefins and dienes.The 2+2 cycloaddition of vinyl ketene 2 with olefins was regiospecific and afforded 2-vinylcyclobutanones.In some cases thermolysis and photolysis lead to different stereoisomers.Trapping of 2 with siloxydienes gave 4-pyranones by a stepwise process.Comparison between the two methods reveals that photolysis was a cleaner route to 2-vinylcyclobutanones than thermolysis. photolysis, 2+2 cycloaddition, vinyl ketenes, cyclobutanones