A computational study of the formation and dimerization of benzothiet-2-one

Dhandapani V. Sadasivam, David M. Birney

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(Chemical Equation Presented) A computational B3LYP/6-31G(d,p) study of the formation of benzothiet-2-one (4) from benzothiophenedione (2) and its subsequent dimerization to 5 was performed. The proposed intermediate ketene 3 has no gas-phase barrier to ring closure to 4. Three transition structures for dimerization were located. The geometry of the lowest energy one (TS8a) has a geometry corresponding to a two atom + two atom, face-to-face addition of the two thiolactone moieties. The orbital interactions suggest that the reaction is pseudopericyclic.

Original languageEnglish
Pages (from-to)245-248
Number of pages4
JournalOrganic Letters
Issue number2
StatePublished - Jan 17 2008


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