JOURNAL of the Tunisian Chemical Society

serving the Research, the Education and the Industry

Sterochemical aspects of cope rearrangement of diethyl 1,5 hexadienes

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Stereospecific synthesis of heterosubstituted 1,5 hexadienes is realised. These diethers rearrange preferentially through a chair transition state. The contribution of the boat transition state is detected. The Z/E olefinic bond ratio of the dienol ethers obtained reveals that the reaction is not governed by the free energy change for the conversion of a substituent from the equatorial to the axial position but rather by the relative thermodynamic stability of the isomers Z.Z. and E.E.

R. Abdelhedi, M.L. Bouguerra, J.C. Pommelet, J. Chuche

Pages 7-13

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