Cyclohexerie-3-01 acetate was readily made fro111 cyclohesene and when oxidized, preferably with performic acid, gave 20 to 25y0 yields of partly acylatecl cis-cis-trans-cyclol~exane-1,2,3-triol, but only 1 to 27, oT the cis-trans-cis isomer. The striictures of the three cyclohexa~~e-1,2,3-triols were deduced froin the theory of the Walclen Inversion.

Abstract

Satisfactory preparations, from hydroquinone and its monomethyl ether respectively, were devised for the above cornp'ounds which were thought to be new.The methyl ether of 4-hydroxycyclohexene was a n oil, n y 1.4566, boiling a t 136OC.; the uncrystallized benzoate had nn, 1.5360 and b.p. 14g°C. at 12 nun.pressure.

The first part of this paper is concerned with a quantitative investigation of the reaction of various polynuclear aromatic hydrocarbons with maleic anhydride. In the second part a micromethod for the separation of mixtures of polynuclear aromatic hydrocarbons, based on this reaction, is described. These studies were undertaken in anticipation that such mixtures might occur in carcinogenic extracts from biological sources.