Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones

Alfred Hassner, Simha Naidorf

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


4,4-Dich1oro-2-cyclobutenones 1, available by cycloaddition of acetylenes to dichloroketene, can be photolyzed in the presence of olefins or dienes to produce regiospecifically 2-vinylcyclobutanones 3-11. The photochemical reaction succeeds even in some cases where thermolysis fails and was shown to proceed by electrocyclic ring opening to a vinylketene. Stereochemically the results of photolysis of 1 differ from thermolysis with identical olefinic substrates.

Original languageEnglish
Pages (from-to)6389-6392
Number of pages4
JournalTetrahedron Letters
Issue number52
StatePublished - 1986

Bibliographical note

Funding Information:
Support of this research by a grant from the Israel Academy of Sciences


Dive into the research topics of 'Photochemical generation of vinylketenes by electrocyclic opening of cyclobutenones'. Together they form a unique fingerprint.

Cite this