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Letter

A Computational Study of the Formation and Dimerization of Benzothiet-2-one

Supporting Info

Dhandapani V. Sadasivam and David M. Birney*

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061

Org. Lett., 2008, 10 (2), pp 245–248

DOI: 10.1021/ol702628v

Publication Date (Web): December 20, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, david.birney@ttu.edu

Abstract

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.

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