The Journal of Organic Chemistry

Cyclobutane-bicyclobutane system. 11. Mechanism and stereochemistry of general acid-catalyzed additions to bicyclobutane

S Hoz, M Livneh, D Cohen

Index: Hoz, Shmaryahu; Livneh, Mordechai; Cohen, Drora Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4537 - 4544

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Citation Number: 10

Abstract

Department of Chemistry, Bar-Zlan University, Ramat-Gan 52100, Zsrael Received July 30, 1986 ... The electrophilic addition of MeOH across the central bond of 3-X-bicyclobutanecarbonitriles (X = H, Me, C1) was found to be a general acid catalyzed reaction with Br0nsted a = 0.96. The p+ value of these reactions is -7.1 f 1.3. These two coefficients are interpreted as an indication of an unbalanced transition state. In the case of X = H and Me, the addition reaction is of ...