Rearrangement pathways of the tricyclo[4.1.0.01,3]heptyl skeleton

Article abstract of DOI:10.1016/S0040-4039(97)10092-2

Syn- and anti-1-methyltricyclo[4.1.0.0^4,6]heptan-2-ol derivatives (4a and 4b) have been prepared. Their buffered solvolyses in anhydrous 2,2,2- trifluoroethanol were studied. Anti dinitrobenzoate 4a solvolyzes to give mainly m-xylene and two trifluoroethyl ethers (5 and 6). Solvolysis of the syn mesylate 4b gives 6-methyl-1-(2,2,2- trifluoroethoxy)tricyclo[4.1.0.0^3,5]heptane (7), the product of a solvent trapped cyclopropyl cation.