Diels-AIder Reactions of 5, 5, 5-Trichloro-3-penten-2-one and Related Compounds

S Tsuboi, Y Ishiguro, A Takeda

Index: Tsuboi,S. et al. Bulletin of the Chemical Society of Japan, 1974 , vol. 47, p. 1673 - 1677

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Citation Number: 8

Abstract

The Diels-AIder reaction of 5, 5, 5-trichloro-3-penten-2-one (1a) with cyclopentadiene afforded exo-2-acetyl-endo-3-trichloromethylbicyclo [2.2. 1] hept-5-ene (2a) stereoselectively. The stereochemistry of the reactions of cyclopentadiene with several γ- chlorinated α, β-unsaturated ketones was examined. The endo-directive abilities decreased in the following order: CCl 3> CCl 2 CH 3, CHCl 2, CCl (CH 3) 2> CH (CH 3) 2> CH 3. ...