A physicochemical study of isocoumarin, 3,4-dihydroisocoumarin, and bis-3,4-dihydroisocoumarin by dipole moment, infrared, ultraviolet, and polarographic measurements

Abstract

Hydrogen abstraction, by t-butoxyl radicals, from 3,4-dihydroisocoumarin, produces radicals which dimerize to give bis-3,4-dihydroisocoumarin in one of two possible diastereoisomeric forms. This is shown by dipole moment measurements to be the meso form. I.r. measurements support this assignment. The dipole moments of the related compounds isocoumarin and 3,4-dihydroisocoumarin are reported. The results of a polarographic and u.v. spectral study of isocoumarin are also discussed.