Studies on Cycloaddition of Cyclohexa-2,4-dienones and Transformation of Adducts: A General, Stereoselective Route to Multifunctional Bicyclo[2.2.2]octanes and Diquinanes

Abstract

The cycloaddition of in situ generated cyclohexa-2,4-dienones with vinyl ethers, vinyl acetate, and phenyl vinyl sulfone leading to variously functionalized bicyclo[2.2.2]octanes has been examined. Functional group manipulation in the resulting adducts gave bicyclo[2.2.2]octanes endowed with a β,γ-enone chromophore. Triplet-sensitized irradiation of bicyclooctenones followed by reductive cleavage provided a stereoselective route to diquinane frameworks having diverse functionalities.

Key words

Diels-Alder reaction - photochemistry - pericyclic reaction - rearrangements

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13

Crystal data 7b: C₁₃H₁₉O₃Cl, MW 258.09, space group, monoclinic, P2₁/c, a = 10.256(2), b = 7.6274(12), c = 15.360(7) Å, α = 90.0, β = 107.44(3), γ = 90.0˚, U = 1146.3(6) A^³, Z = 4, D _c = 1.218 g/m^³, T = 293(2) K, F(000) = 456, size = 0.26 × 0.16 × 0.12 mm. Reflections/collected/unique 10532/2012 [R(int) = 0.0258], final R indices [I >2σ(I)] = R1 = 0.0369, wR2 = 0.105c, R indices (all data) R1 = 0.0554, wR2 = 0.1107. The complete crystal data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif quoting the CCDC number 674959.

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Crystal data 11c: C₁₇H₁₉ClO₄S, MW 354.83, space group, monoclinic, P2₁/c, a = 8.3197(6), b = 23.0608(19), c = 15.360(7) Å, α = 90.0, β = 96.045(6), γ = 90.0˚, U = 1600.8(2) A^³, Z = 4, D _c = 1.472 mg/m^³, T = 120(2) K, F(000) = 744, size = 0.33 × 0.27 × 0.21 mm. Reflections/collected/unique 8932 / 2801 [R(int) = 0.0732], final R indices [I >2σ(I)] = R1 = 0.0826, wR2 = 0.2139, R indices (all data) R1 = 0.0965, wR2 = 0.2226. The complete crystal data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif quoting the CCDC number 674960.