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Synfacts 2008(1): 0034-0034  
DOI: 10.1055/s-2007-992397
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

An Unexpected Bromine-Catalyzed Dimerization of Tetrathiafulvalene (TTF) Derivatives

Contributor(s): Timothy M. Swager, Gaku Fukuhara
H. Gopee, B. M. Petersen, A. D. Bond, J. O. Jeppesen*
University of Southern Denmark, Odense, Denmark
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

The authors discovered an unanticipated type of dimerization of dihalo-TTFs 3 during their synthesis (outlined in the scheme). For obtaining crystals of 3, a sample of 3a was dissolved in CH2Cl2-MeOH, resulting in the formation of 4a as judged from MALDI-MS, NMR, and X-ray structural analyses. In contrast, the formation of 4b needs a catalytic amount of bromine, indicating the dimeri­zation is apparently catalyzed by Br2.