Toluene as a novel carrier of xanthates—preparation,use and surrogate of S-tri- and di-chloromethyl xanthates |
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Authors: | Raphaë l Dumeunier,Annika Huber |
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Affiliation: | Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland |
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Abstract: | Toluene has been identified as a novel carrier of xanthates. Their corresponding fragmentative precursors proved to behave efficiently in radical group transfer reactions. As examples, unprecedented S-tri/di-chloromethyl xanthates could be prepared, isolated and further used in radical additions to olefins. Their precursors (de-aromatized toluene upon which is grafted, at one end, a tri/di-chloromethyl-group and, at the other end, a dithiocarbonyl group) can also be used directly in the transfer of both groups to olefins. The re-aromatizing loss of toluene by radical initiated fragmentation of the precursors brings thus new opportunities to the chemistry of xanthates, exemplified here in the intermolecular additions to olefins of new S-tri/di-chloromethyl xanthates. |
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Keywords: | Rearomatization Radical chain Fragmentation Xanthate Transfer reaction |
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