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2005
Cyclopentane derivatives
Q 0030
Thermal and Palladium-Catalyzed [3 + 2] Synthesis of Cyclopentadienone Acefrom Cyclopropenone Acetals and Acetylenes. — Substituted cyclopropenone
04- 078 tals
acetals are shown to undergo thermal or palladium-catalyzed [3 + 2] cycloaddition to
electron-deficient acetylenes to give a variety of new substituted cyclopentadienone derivatives. The catalyzed reaction is generally higher yielding than the thermal reaction
and sometimes complementary [cf. →(VIII)/(IX)]. The present reaction provides a
unique example of a [3 + 2] reaction rather than a [1 + 2] cycloaddition reaction leading
to three-membered rings that is the only reaction type thus far observed. The utility of
the new cyclopentadienone acetals is illustrated by their Diels—Alder reaction with
olefins furnishing bicycloheptenes [cf. (XV)] and a formal [2 + 2 + 2] construction of
a substituted benzene (XVIII). — (ISOBE, H.; SATO, S.; TANAKA, T.;
TOKUYAMA, H.; NAKAMURA*, E.; Org. Lett. 6 (2004) 20, 3569-3571; Dep.
Chem., Univ. Tokyo, Bunkyo, Tokyo 113, Japan; Eng.) — Steudel
2005
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