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Generation by retro-ene reaction of cyclohex-2-enethione and cyclopent-2-enethione

✍ Scribed by Emmanuelle Briard; Yves Dat; Jocelyne Levillain; Jean-Louis Ripoll

Book ID
104258362
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
138 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 -80Β°C in the condensed pha~, have been characterized by UV-visible and IR spectroscopy at -196Β°C, as well as, in the gas pha~,;e, by direct FVT/HRMS coupling. The reaction of 2 with diazomethane in THF led to 1,3-dithioh'me 9.

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