Transpositions thermiques de derives d'α-pinene |
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Authors: | Yvonne Bessiere Claude Grison Ginette Boussac |
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Institution: | Laboratoire de Chimie de l''Ecole Normale Supérieure associé au CNRS, 24 rue Lhomond, F 75231 Paris Cédex 05, France |
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Abstract: | Novel thermal transformations of (+)-pin-2-en-9-al 1 and (+)-9-methyl-pin-2-en-9-one 3 by 3,3] sigmatropic mechanism to allyl vinyl ethers 2 and 4 are described. The ether 4 may undergo further rearrangement in an acid-catalysed step to the (-)-2.6-dimethylbicyclo3.3.1]non-6-en-2ones (5 and 5'). Formation of the bicyclic ketones (+)-5 and 5' of opposite absolute configuration occurs by 3,3] sigmatropic rearrangement of the trimethylsilyl enol ether of 3 and hydrolysis. The proposed mechanism is confirmed by studying the deuterated ketone d3?3. |
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