Journal of the Chemical Society. Perkin transactions I p. 1869 - 1874 (1984)
Update date:2022-08-04
Topics:
Katada, Tomonori
Eguchi, Shoji
Esaki, Toshiyuki
Sasaki, Tadashi
The thermal cycloaddition reaction of adamantanethione (1) with α,β-unsaturated carbonyl compounds such as acrolein, methacrolein, and methyl vinyl ketone occurred smoothly at 80 - 140 deg C to afford, regioselectively, adamantane-2-spiro-2'-(1'-oxa-3'-thiacyclohex-5'-enes) (3a-e) as novel <4 + 2> cycloadducts in good yield.The nature of this cycloaddition is discussed on the basis of kinetics, solvent effects, and FMO theory.
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