trans-Cycloalkenes. Part III. Stereochemistry and mechanism of some reactions of diastereoisomeric 3-substituted trans-cyclo-octenes

Abstract

Three types of process are described: (i) the stereospecific addition of acetic acid to (1RS,2RS)-trans-cyclo-oct-2-enyl acetate to give cis-cyclo-octane-1,3-diol diacetate, (ii) the reaction of (1RS,2RS)- and (1SR,2RS)-trans-cyclo-oct-2-enyl methyl ethers with n-butyl-lithium to give (1RS,3RS)-3-butyl-trans-cyclo-oct-1-ene and 3-butyl-cis-cyclo-oct-1-ene, respectively, and (iii) the thermal interconversion of the diastereoisomeric acetates at 167° to give an equilibrium mixture comprising 84% of the (1RS,2RS)- and 16% of the (1SR,2RS)-form.