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

Vishwakarma Singh; Girish Chandra; Shaikh M. Mobin

doi:10.1055/s-2008-1067203

PAPER

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

Vishwakarma Singh*^a, Girish Chandra^a, Shaikh M. Mobin^b
^a Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India
^b National Single X-ray Diffraction Facility, Indian Institute of Technology Bombay, Mumbai 400076, India
e-Mail: vks@chem.iitb.ac.in;

Abstract

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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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Referenzen

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