62609-28-3Relevant academic research and scientific papers
Allylic Displacements and a Novel Ester-Ether Interchange in Fused Cyclobutanones
Hassner, Alfred,Dillon, John
, p. 3315 - 3319 (2007/10/02)
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.
EFFECT OF CONFORMATION AND STEREOCHEMISTRY IN SUBSTITUTION REACTIONS OF FUSED CHLOROCYCLOBUTANONES: OXYALLYL CATION INTERMEDIATES
Hassner, Alfred,Dillon, John L.,Krepski, Larry R.,Onan, Kay D.
, p. 1135 - 1138 (2007/10/02)
Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguosly established by X-ray analysis, undergo an unususal displacement with methoxide as nucleophile to produce α-methoxycyclobutanones.The success of this reaction, whi
