A new route to the rare tricyclo[3.3.1.02,7]nonane skeleton. Synthesis of 1,2,3,4,7-pentafluorotricyclo[3.3.1.02,7]non-3-ene-8,8-diol hemihydrate via thermolysis of pentafluorophenyl prop-2-enyl ether, and related studies

Abstract

Prolonged heating of pentafluorophenyl prop-2-enyl ether (1) in the vapour phase at 137–141 °C and hydration of the product gives a compound (10) incorporating the rare [3.3.1.0^2,7]nonane ring skeleton and containing a plane of symmetry. An analogous reaction occurs with pentafluorophenyl 2-methylprop-2-enyl ether. Some reactions of (10) are described.