Areces, Pilar, Ávalos, Martín, Babiano, Reyes, Cintas, Pedro, González, Luis, Hursthouse, Michael B., Jiménez, José L., Light, Mark E., López, Ignacio, Palacios, Juan C. and Silvero, Guadalupe (2001) Synthesis of dihydrothiophenes by an amino-directed thioisomünchnone-alkene cycloaddition reaction. European Journal of Organic Chemistry, (11), 2135-2144. (doi:10.1002/1099-0690(200106)2001:11<2135::AID-EJOC2135>3.0.CO;2-L).
Abstract
Dihydrothiophenes can easily be obtained by a general protocol involving the reaction of 2-aminothioisomunchnones with electron-deficient alkenes. The overall process can be interpreted as a sequential [3+2] cycloaddition/ring-opening cyclization reaction. The structures of the products could be unequivocally assigned by X-ray diffraction analysis. A theoretical study at a semiempirical level (PM3) with a further single-point refinement of energies at the B3LYP/6-31G(*) level also offers mechanistic insights into the stereochemical outcome.
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