Construction of Extended and Polymeric 1,3-Dithiolane and Tetrathiafulvalene Derivatives using Cycloaddition of Bun 3P.CS2 |
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Authors: | R Alan Aitken Lawrence Hill Tracy Massil |
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Abstract: | Abstract Cycloaddition of the adduct between Bun 3P and CS2 to strained double bonds such as in norbornene gives novel zwitterionic products such as 5. This dissociates to the ylide 4 so that carrying out the reaction in the presence of an aldehyde leads to a Wittig reaction to give 2-alkylidene-1,3-dithiolanes. The compound 5 reacts with acetylenic dipolarophiles by cycloaddition accompanied by loss of Bun 3P to give dihydro-TTF derivatives. Both these reaction types also occur for norbornadiene and by using this together with dialdehydes or diacetylenes a range of new sulfur-rich extended and polymeric structures have been obtained. |
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