Journal of Organic Chemistry p. 4160 - 4166 (1995)
Update date:2022-08-04
Topics:
Diaz-Ortiz, Angel
Diez-Barra, Enrique
Hoz, Antonio de la
Prieto, Pilar
Moreno, Andres
et al.
(R)-4-Phenyl-2-methylene-1,3-dioxolane (1) undergoes 1,3-dipolar and Diels-Alder cycloadditions under microwave irradiation within 3 min with excellent yields, a simple purification procedure, and an interesting facial selectivity.The stereochemistry of these cycloadducts has been inferred by NOESY experiments and molecular mechanics calculations.X-ray structure determination was required in one case.Thermal isomerization of the cycloadducts was performed affecting only the spiro-carbon.The Diels-Alder adducts in the presence of a slight amount of acid yield the corresponding open chain esters.
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