Tetrahedron letters

Lithiated cyclopropanone ketals

P Dowd, C Kaufman, P Kaufnan, YH Paik

Index: Dowd, Paul; Kaufman, Christopher; Kaufman, Paul; Paik, Yi Hyon Tetrahedron Letters, 1985 , vol. 26, # 19 p. 2279 - 2282

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Citation Number: 3

Abstract

Abstract The ketene acetal I reacted with dibromocarbene yielding the dibromocyclopropanone ketal II, which was reduced to the monobromide III by treatment with tri-n-butyltin hydride. Reaction of III with n-butyllithium at− 78 C yielded the lithiated cyclopropanone ketal IV, which yielded adducts with acetone, cyclohexanone, cyclohexenone, 3, 3, 3-trimethoxybutan-2-one, 2-butanone, and 3-pentanone.