High pressure and thermal Diels-Alder reactions of 5-nitro[2.2]paracyclophanepyran-6-one |
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| Authors: | Lucio Minuti Assunta Marrocchi Mirko Seri |
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| Affiliation: | a Dipartimento di Chimica, Università degli Studi di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
b Central Institute for Chemistry, Hungarian Academy of Sciences, PO Box 17, H-1525 Budapest, Hungary |
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| Abstract: | The Diels-Alder reactions of 5-nitro[2.2]paracyclophanepyran-6-one with 1,3-butadienes and 1,2-dihydro-3-vinyl-naphthalene were examined under thermal and high-pressure conditions. The cycloadditions with 1,3-butadienes occurred in good yield and anti-exo diastereoselectively only under high-pressure conditions; the one with 1,2-dihydro-3-vinyl-naphthalene afforded comparable yields of mixtures of anti/syn adducts under normal and high-pressure conditions. A structural analysis of the reaction products by 1H and 13C NMR spectroscopy is presented. |
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| Keywords: | [2.2]Paracyclophanes Coumarins High pressure Diels-Alder cycloaddition |
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