67437-45-0Relevant academic research and scientific papers
The Preparation and Photolysis of (E)-1-Aryl-3-methyl-3-phenylbut-1-enes
Blunt, John W.,Coxon, James M.,Robinson, Ward T.,Schuyt, Helen A.
, p. 565 - 579 (2007/10/02)
Reaction of 2-methyl-2-phenylpropylmagnesium chloride with benzaldehyde in tetrahydrofuran gave, 2,7-dimethyl-2,4,5,7-tetraphenyloctane-4,5-diol as a 1:2 mixture of clear transparent crystalline plates (meso) and needles (+/-), 3-methyl-1,3-diphenylbutan-1-one, benzyl alcohol, 2-methyl-2-phenyl-propane and a low yield of 3-methyl-1,3-diphenylbutan-1-ol.The distinction between the meso- and the (+/-)-diols was unequivocal because the unique space group of the former requires the dimeric molecules to lie about a crystallographic centre of symmetry.The mechanism involved in the formation of the products of the Grignard reaction is examined.By careful choice of reaction conditions a series of 1-aryl-3-methyl-3-phenylbutan-1-ols were prepared.Dehydration of the 1-aryl-3-methyl-3-phenylbutan-1-ols with p-toluenesulfonic acid and a short reaction time gives (E)-1-aryl-3-methyl-3-phenylbut-1-enes but longer reaction times afford 3-aryl-1,1-dimethylindanes.Photolysis of the (E)-1-aryl-3-methyl-3-phenylbut-1-enes affords (Z)-1-aryl-3-methyl-3-phenylbut-1-enes and trans-1-aryl- 3,3-dimethyl-2-phenylcyclopropanes.Extended photolysis gives 4-aryl-2-methyl-3-phenylbut-1-enes via trans-1-aryl-3,3-dimethyl-2-phenylcyclopropane by rupture of the cyclopropyl bond adjacent to the aryl substituent.
