On β-Monobromohinokitiol

Abstract

From its structural standpoint1~2~, hinokitiol (4-isopropylcycloheptatriene-2, 4, 6-ol-2-one-1) is liable to undergo electrophilic substitution at 3, 5 and 7 (i. e., o, p and o' proposed by the authors). It follows, therefore, that hinokitiol would give 3 kinds of monoand di-substituted, and one of tri-substituted bromination products, Nozoe, Sebe and their coworkers3~ carried out the bromination of hinokitiol under various conditions, and obtained one kind of monobromo compound (m. p. 56), two kinds of dibromo compounds (a m.p. 134; ,8: m. p. 96), and one kind of tribromo compound (m. p. 88). From the course of formation of these compounds3~, and the measurement of dipole moments2~, it was assumed that monobromo compound (m. p. 56) was substituted at 7 or o' (I), a-and / -dibromo compounds at 3, 7 (o, o') (II), and at 5, 7 (o', p) (III), respectively.