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Synthesis 2001; 2001(3): 0409-0412
DOI: 10.1055/s-2001-11434
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Generation and Trapping of α,β-Unsaturated Thioketones. Synthesis of 5,6-Dihydrothiopyranes

Giuseppe Capozzi* , Silvia Giacomelli, Stefano Menichetti, Cristina Nativi
  • *Centro C.N.R. “Chimica dei Composti Eterociclici”. Dipartimento di Chimica Organica, Universitá di Firenze. Via G. Capponi 9, 50121 Firenze, Italy; Fax + 39(0 90)39 38 95; E-mail: menichet@isengard.unime.it
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Publication Date:
31 December 2001 (online)

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The transformation of the ketone group of compound 5 into the corresponding methylenic group in 6 allowed the thermal retro Diels-Alder generation of α,β-unsaturated thioketone 7, which reacts as heterodiene or heterodienophile to give 5,6-dihydro-4H- or 2H-thiopyran derivatives 12-15 and 17, respectively.

thioketones - hetero Diels-Alder reaction - retro Diels-Alder reaction - sulfur heterocycles - regioselectivity