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Paper | Regular issue | Vol 26, No. 4, 1987, pp.969-988
Published online, 1st January, 1970
DOI: 10.3987/R-1987-04-0969
Interaction of Thietes with Electron-deficient Molecules

Sharon Marinuzzi-Brosemer, Bhalchandra H. Patwardhan, Kenneth A. Greenberg, and Donald C. Dittmer

*Department of Chemistry, Syracuse University, Syracuse, New York 13244-1200, U.S.A.

Abstract

Thietes (thiacyclobutenes) give substituted 1,4-benzodioxanes when treated with the o-quinones, o-chloranil and o-bromanil, but dehydrogenation occurs vith the p-quinane, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), as indicated by the formation of the hydroquinone in good yield. Colored solutions are formed when thietes are mixed with the electron acceptors DDQ, tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ). The stoichiometry of the charge transfer complexes appears to be 1:1 (donor:acceptor) according to Job plots. Formation constants do not vary greatly from complex to complex. Blue-black solids have been obtained from thietes and TCNQ. The material obtained from 2H-thiete is electrically conducting - a semiconductor - but that from 3-phenyl-2H-thiete is an insulator. Several of the isolated charge-transfer complexes give satisfactory elemental analyses for 1:1 complexes and most of them give broad electron spin resonance spectra.