Silver (I)-catalyzed rearrangement of bicyclobutanes. Mechanism. II

S Masamune, M Sakai, HH Westberg…

Index: Sakai,M. et al. Journal of the American Chemical Society, 1971 , vol. 93, p. 4611 - 4613

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Abstract

0 2 equiv of pyridine at 70”.* 2 equiv of 1, 5-diazabicyclo [4.3. 0]-non-Sene. Bicyclobutane (0.3 M) with AgClOa (0.1 M) in benzene at 25”. dDetermined by glpc using cyclohexane as reference. two different reactions, Ag (1)-bicyclobutanes and the elimination reaction of cyclopropylcarbinyl mesylates, are remarkably similar. Compound 9 was converted exclusively into 5, and not into 4.7 exo, exo-2, 4-Dimethylbicy~ lobutane~ and mesylate ( ...