No abstract

In their study of the antiseptic properties of phenolic sulfur combinations, Hilbert and Johnson2 3discovered that ^-hydroxydiphenyl sulfide possessed greater germicidal power than was then shown by the most active members of the alkylated phenol family. Since this unusual activity appeared to be due largely to the sulfur linkage, it was felt by the authors that even more striking results might be obtained by substituting an alkyl group for one of the phenyl groups in this compound. Accordingly, they undertook the synthesis of a series of hydroxy-phenyl alkyl sulfides of which a number are described in this paper.

substituted phenols and germicidal activity 1195 aniline was converted into the m-nitro-sec.-butylbenzene in the usual manner by diazotization in alcohol:6 «z-nitro-sec.-butylbenzene; b. p. 132-134°(19 mm.). Anal. Caled.: N, 7.8. Found: N, 8.0. This was reduced to the amine with tin and hydrochloricacid: m-s^c.-butylaniline, b. p. 120°( 18mm.

On the basis of spectroscopic evidence structures (4), (5), (7) and (8) respectively are assigned to the neolignans eupodienone-4, -5, -6 and -7 isolated from Eupomatia laurina R.Br. The products of dienone-phenol and dienol-benzene rearrangement of the substances are characterized.

Rearrangement of eupodienone-1 and derivatives, including certain dienols, under a variety of acidic conditions produced dibenzocyclooctene derivatives. Spectroscopic evidence and chemical degradation showed that in the rearrangements alkyl rather than aryl group migration had occurred. The stereochemistry of the products is discussed.