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The title compounds la-3c were prepared by stereoselective reduction of the respective dibromides. Pyrolysis gave allylic bromides (8, 9, 11) as primary and dienes (10, 12) as secondary products. Product ratios were independent of the stereochemistry of the starting materials. No differences of the rearrangement rates of the stereoisomers were observed in gas phase reactions of the derivatives of bicyclo[6.1.0]- and bicyclo[8.1.0]alkanes. With the larger bicyclo[10.1.0] derivatives, however, distinct differences in the thermal stability of cis-trans-isomers4c/5c or 2c/3c were found in condensed phase.

Preparation and Pyrolysis of Stereoisomeric Bromobicyclo[n.1.0]alkanes ( n = 6, 8 , 10)