Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 53, Issue 5, Pages 518-525Publisher
SPRINGER
DOI: 10.1007/s10593-017-2086-9
Keywords
cyclic sulfones; 3,6-dihydro-2H-thiopyrans; thioketones; reaction mechanisms; thia-Diels-Alder reactions
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Funding
- National Science Center (Cracow, PL) [Dec-2012/06/A/ST5/00219]
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Dihetaryl thioketones possessing thiophen-2-yl and selenophen-2-yl rings react as ''superdienophilic'' reagents with nonactivated 1,3-dienes such as 2,3-dimethylbuta-1,3-diene, cyclopentadiene, and mixtures of isomeric hexa-2,4-dienes to produce the expected 2H-thiopyrans in moderate to excellent yields. In the latter case, the corresponding cis-2,2-dihetaryl-3,6-dimethyl-3,6-dihydro-2Hthiopyrans are formed as the sole products in a stereoconvergent thia-Diels-Alder reaction. A stepwise mechanism via delocalized diradical intermediates is postulated to rationalize the observed reaction course. Treatment of 4,5-dimethyl-2,2-di(thiophen-2-yl)3,6-dihydro-2H-thiopyran with excess of m-CPBA at room temperature leads to the oxidation of the C-C bond and the sulfur atom in the six-membered ring.
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