α-LongifoIene C15H24F1, a tricyclic sesquiterpene hydrocarbon, and phenol were reacted in the presence of boron trifluoride as a catalyst. 1.The reaction was carried out without or with various kinds of solvent under various conditions, changing temperature and time of reaction, but there was no striking difference on the kind of products and their yields. 2. About one-half of α-longifolene was left unreacted with phenol and isomerited to isolongifolene. 3.A dextro-rotatory compound, bp.178-183°C/5mm Hg, was obtained in 30% yield and this was assumed to be longifolyl phenyl ether from the infrared absorption spectrum and other tests.
A mixture of rongibornyl chloride, a hydrogen chloride additive product of longifolene, and was condensed with a large amount of phenol by heating. The reaction products were longibornyl phenyl ether, columns, mp.90.7-91.5°C, and a viscous fluid which was assumed to be a mixture of o-and p-longibornylphenol. It was found that the transition of longibornyl phenyl ether into longibornylphenol was possible in the presence of acidic catalyst.
Catalytic reduction of disulfides consisting of a pair of the same octyl, dodecyl, benzyl, phenyl or p-tolyl radicals was carried out with molybdenum trisulfide catalyst and hydrogen with an initial pressure at around 100 atm at various temperatures. Each of these disulfides showed the cleavage of S-S bond at 130-140°C and gave mercaptans with good yield.The mercaptans formed in the intermediate stage were further decomposed at above 200°C to give hydrocarbons and the cleavage was almost completed at around 300°C.The same results were obtained by use of mercaptans as the sample.
In order to clarify the effect of X on the reactivity of active chlorine atom in chloro-S-triazine derivatives having substituent groups, the reaction between A-type chloro-S-triazine derivative, and aniline has been investigated.The result of comparison of reaction velocities indicated that the reactivity of A was decreased in the order of The effect of X was mainly due to its polar effect, this was considered to be transmitted to the reacting position of s -triazine nucleus through an oxygen atom. Accordingly, it was clarified that an electron-attractive group X had a tendency to proceed the reaction of aniline easily while the X having an electron-donating property retarded the reaction.Also, the reaction between A (X=H) and type aniline substituent has been investigated.It was found that the reactivity of aniline was decreased in the order of Thus, there was a regularity that the electron-donating group in A caused an increase in the reactivity of aniline while the electron-attractive group decreased the reactivity.