Dimers of α,β-substituted styrenes: Tetralin derivatives from reaction of 1-(p-Chlorophenyl) -2,2-dimethylpropan-1-ol with sulphuric acid

Abstract

Two compounds, m.p. 129-130º and 169-170°, obtained from reaction of 1-(p-chlorophenyl)-2,2-dimethylpropan-1-ol or from 2-(p-chlorophenyl)-3-methylbut-2-ene with sulphuric acid, have been shown to be the diastereoisomers of 7-ohloro-3-(p-chlorophenyl)- 1 -isopropyl- 1,4,4-trimethyltetralin (6a). Reaction of mono- and di-methyl-p-chlorostyrenea with sulphuric acid under the same conditions gave mainly indane derivatives. Products were separated by fractional crystallization, and preparative gas chromatography. Structures of pure compounds were assigned mainly on the basis of n.m.r, spectroscopy.