2,4-Dioxopentane-3-thione la reacts as an enophile with various allyl derivatives affording thiophilic ene adducts as single regioisomers with high (E) stereoselectivity. Using allyl ethers or allenes as ene counterparts, the formation of the thiophilic adduct is followed by a fast cycloaddition reaction in which la behaves as a diene or a dienophile, respectively.
alpha ',alpha '-dioxothiones, III Regio- and stereoselective ene and tandem "ene-cycloaddition'' reactions of 2,4-dioxopentane-3-thione / G. Capozzi; M. Fragai; S. Menichetti; C. Nativi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 1999:(1999), pp. 3375-3379.
alpha ',alpha '-dioxothiones, III Regio- and stereoselective ene and tandem "ene-cycloaddition'' reactions of 2,4-dioxopentane-3-thione
CAPOZZI, GIUSEPPE;FRAGAI, MARCO;MENICHETTI, STEFANO;NATIVI, CRISTINA
1999
Abstract
2,4-Dioxopentane-3-thione la reacts as an enophile with various allyl derivatives affording thiophilic ene adducts as single regioisomers with high (E) stereoselectivity. Using allyl ethers or allenes as ene counterparts, the formation of the thiophilic adduct is followed by a fast cycloaddition reaction in which la behaves as a diene or a dienophile, respectively.
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