Abstract

Elimination reactions of 2-substituted-1,2-diphenylpropanes are described. It is shown that dehydrations, dehydrohalogenations and deaminations of the appropriate compound produce alkene mixtures containing 45–55 % of α-benzylstyrene. This alkene is shown to be the least stable of the isomeric trio α-benzylstyrene, cis and trans-α-methylstilbene by isomerization studies. Studies of the dehydration include the 1-phenyl-2-( p-substituted phenyl)-2-propanols which show the same characteristics as the unsubstituted alcohol. On the basis of the effect of substituents on the rate of dehydration, it is suggested that these eliminations proceed through a carbonium ion like transition state. The composition of the initially formed alkene is then determined by the steric size of the groups attached to the reaction centre.

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