Tetrahedron Letters p. 2279 - 2282 (1985)
Update date:2022-08-05
Topics: Cyclization Lithiation Ketals Cyclopropanone
Dowd, Paul
Kaufman, Christopher
Kaufman, Paul
Paik, Yi Hyon
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 degC yielded the lithiated cyclopropanone ketal IV, which yielded adducts with acetone, cyclohexanone, cyclohexenone, 3,3,3-trimethoxybutan-2-one, and 3-pentanone.
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