Journal of Organic Chemistry p. 3315 - 3319 (1986)
Update date:2022-08-05
Topics:
Hassner, Alfred
Dillon, John
Chlorophenylcyclobutanone 11, prepared by chlorophenylketene addition to cyclohexene, reacts readily with simple and hindered carboxylic acids in a cine substitution to produce keto esters 14.The acyloxy and phenyl substituents in 14c are shown by X-ray diffraction to be cis oriented; nevertheless 14 reacts with NaOMe at 20 deg C by an unusual ester-ether interchange to produce 15 and the released carboxylate RCO2-.These reactions apparently proceed via an oxyallyl cation intermediate.The behaviors of related cyclobutanones 4, 6, and 11 with methoxide are contrasted.
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