Perhydroazulenes. 5. Preparation of Perhydroazul-9(10)-en-4-one

Article abstract of DOI:10.1021/jo00174a025

An improved procedure for the preparation of perhydroazul-9(10)-en-4-one is described.Crystal structures were determined for two of the reaction intermediates, 1,6-cyclodecanedione and the cyclic diperoxide derived from 1,6-cyclodecanedione.Measurements of 13C NMR data at various temperatures were used to determine an activation free energy of 14.8 kcal/mol at 298 K for interconversion of the two chair conformers of the cyclic diperoxide.