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2005
Bridged compounds
Q 0060
A Novel and Efficient Synthesis of Bicyclo[2.2.2]octenones and Sigmatropic Shifts
Ground and Excited States: Stereoselective Route to cis-Decalins and Diquinane
25- 067 in
Frameworks. — Treatment of cyclohexadienone dimers of type (I) with the butadiene
equivalent (II) offers a novel route to bicyclooctenones of type (III). On heating, the
latter undergo [3 + 3]-sigmatropic rearrangement providing a novel, general, and stereoselective approach to cis-decalins. Their irradiation in acetone results in formation
of diquinanes via 1,2-acyl shift. — (SINGH*, V.; IYER, S. R.; MOBIN, S. M.;
J. Org. Chem. 70 (2005) 3, 973-981; Dep. Chem., Indian Inst. Technol., Bombay
400 076, India; Eng.) — Jannicke
2005
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