
%0 Journal Article
%A Beckwith, ALJ 
%A Phillipou, G 
%T E2 reactions of menthyl and neoisomenthyl Toluene-p-sulphonates
%J Australian Journal of Chemistry
%D 1976/04/01
%V 29
%N 4
%P 877-882
%K 
%R https://doi.org/10.1071/CH9760877
%U https://www.publish.csiro.au/paper/CH9760877 
%X The reaction of menthyl toluene-p-sulphonate (7) with potassium t-butoxide in benzene-dimethyl sulphoxide proceeds regiospecifically to afford trans-p-menth-2-ene (1). Mixtures of olefins are obtained when sodium ethoxide in ethanol, potassium t-butoxide in t-butyl alcohol or tetrabutylammonium bromide in acetone are used. Neoisomenthyl toluene-p-sulphonate (9), prepared by a stereospecific route from piperitone, affords mixtures of cis-p-menth-2-ene (2) and p-menth-3-ene(3) when treated with strong bases. The results are consistent with the concept of variable E2 transition states. 
