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Report | Regular issue | Vol 24, No. 2, 1986, pp.321-324
Published online, 1st January, 1970
DOI: 10.3987/R-1986-02-0321
Conformational Effects in 1,2-Dithietane, 1,2-Dithiete, 1,3-Dithiole, 2,3-Dihydro-1,4-dithiin and 1,4-Dithiin Radical Cations

Glen A. Russell* and Wing Cheung Law

*Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, U.S.A.


1,2-Dithietane radical cations exist in a nonplanar conformation. With trans-3,4-dimethyl substituents, the barrier to ring flip is >5 kcal/mol. Cyclohexene derivatives 7-10 possess a measurable barrier to ring flip. However, the radical cations 11-16 have a much lower barrier and only conformationally time-averaged ESR spectra are observed at -90°C. The 2,3-dihydro-1,4-dithiin ring of 11 or 19 is conformationally mobile but is locked in a half-chair conformation in 12 and 13.