Tetrahedron Letters p. 8707 - 8708 (1997)
Update date:2022-08-04
Topics:
Briard, Emmanuelle
Dat, Yves
Levillain, Jocelyne
Ripoll, Jean-Louis
The reactive unsubstituted cyclohex-2-enethione (1) and cyclopent-2-enethione (2) have been synthesized in two steps (yields ca 70%) from the corresponding cycloalkenyl bromides. The key step is a retro-ene reaction under FVT conditions. The purple-blue thioketones 1 and 2, polymerizing rapidly above -80°C in the condensed phase, have been characterized by UV-visible and IR spectroscopy at -196°C, as well as, in the gas phase, by direct FVT/HRMS coupling. The reaction of 2 with diazomethane in THF led to 1,3-dithiolane 9.
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