A theoretical study of the [4 + 4] dimerization of thioformylketene

Dhandapani V. Sadasivam, David M. Birney

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


(Figure Presented) A theoretical study (B3LYP and G3MP2B3) of the dimerization of thioformylketene (1) was performed. Four pathways - two [4 + 2] pathways with thioformylketene (1), one [4 + 4] pathway with 1, and one [4 + 2] pathway involving 1 and thietone (11) - were considered. Interestingly, the [4 + 4] pathway with 1 had the lowest barrier (3.8 kcal/mol). The geometry of the transition state TS14 is unusual, with the forming bonds in the plane of the ketene. This suggests that the reaction is pseudopericyclic.

Original languageEnglish
Pages (from-to)5817-5820
Number of pages4
JournalOrganic Letters
Issue number26
StatePublished - Dec 22 2005


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