trans-Cycloalkenes. Part IV. Some aspects of the chemistry of trans-cyclo-octene

Abstract

The following aspects of trans-cyclo-octene chemistry are discussed: (i) proton n.m.r. (including ¹³C–H satellite) data, (ii) rates of addition of 1,3-dipoles, (iii) cyclo-addition of buta-1,3-diene, (iv) rate of epoxidation with peroxy-acid, (v) stereochemistry of addition of [²H₄]acetic acid, and (vi) reaction with benzenesulphenyl chloride. All the results are explicable in terms of the unusual structure of trans-cyclo-octene which possesses a highly torsionally twisted double bond, only one face of which is accessible to attacking reagents.