Reactions of Vinylcyclopropane and Bicyclopropyl Compounds With Maleic Anhydride
Vinylcyclopropane and bicyclopropyl C6 compounds are studied as diene precursors in the Diels-Alder reaction. Their rearrangement under different thermal and microwave conditions leads to specific isomeric hexa-, penta- or butadienes, condensed with maleic anhydride as a dienophile. Adduct stereochemistries were compared to those of previously-synthesized model compounds, and are fully characterized with 2D NMR and GC-MS spectroscopies. Some unsaturated terpenes bearing vinylcyclopropane moieties were also condensed, and their adduct structures assigned.
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| Main Authors: | , , , , , , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedad Química de México A.C.
2009
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| Online Access: | http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S1870-249X2009000400003 |
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| Summary: | Vinylcyclopropane and bicyclopropyl C6 compounds are studied as diene precursors in the Diels-Alder reaction. Their rearrangement under different thermal and microwave conditions leads to specific isomeric hexa-, penta- or butadienes, condensed with maleic anhydride as a dienophile. Adduct stereochemistries were compared to those of previously-synthesized model compounds, and are fully characterized with 2D NMR and GC-MS spectroscopies. Some unsaturated terpenes bearing vinylcyclopropane moieties were also condensed, and their adduct structures assigned. |
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