Project management at the University of Würzburg:
The dimesylates of endo,endo- and exo,exo-bicyclo[1.1.0]butane dimethanol were prepared from benzvalene. The solvolyses of the endo,endo-compound furnished mainly cis-5-substituted cyclopent-2-ene-1-methanol mesylates, which is explained by a heterolytic dissociation with a concomitant Wagner-Meerwein rearrangement. In contrast, the solvolyses of the exo,exo-compound gave nonrearranged products exclusively. Obviously, the Wagner-Meerwein rearrangement does not occur in this case due to the high strain energy of the conceivable intermediate carbocation. This result is inconsistent with a previous finding reported in the literature.
Projekt period: from 01.1999 to 12.2001