Journal
CHEMICAL COMMUNICATIONS
Volume 54, Issue 23, Pages 2850-2853Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc09466c
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Funding
- Ministry of Education and Science of the Russian Federation [4.1154.2017/4.6]
- Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) [UID/QUI/00100/2013]
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The tandem [4+2] cycloaddition between hexafluoro-2-butyne and bis-furyl dienes, like difurfuryl ester, at room temperature leads to the kinetically controlled pincer''-adducts - annulated 4a, 8a-bis(trifluoromethyl) hexahydro-1,4: 5,8-diepoxynaphthalenes. On the other hand, if these reactions proceed at 140 degrees C, only the thermodynamically controlled domino''-adducts - annulated 2,3-bis(trifluoromethyl) hexahydro-1,4: 5,8-diepoxynaphthalenes - are formed. Therefore, a very rare and unexpected example of full kinetic and thermodynamic control in the Diels-Alder reaction is reported in this paper.
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