132595-48-3Relevant academic research and scientific papers
Rhodium-catalyzed allylation of benzyl acetates with allylsilanes
Onodera, Gen,Yamamoto, Eriko,Tonegawa, Shota,Iezumi, Makoto,Takeuchi, Ryo
scheme or table, p. 2013 - 2021 (2011/10/09)
Benzyl acetate reacted with allyltrimethylsilane to give an allylation product in the presence of a catalytic amount of the (cyclooctadiene)rhodium(I) chloride dimer {[Rh(cod)Cl]2}, sodium tetrakis[3,5- bis(trifluoromethyl)phenyl]borate (NaBARF), and triphenyl phosphite [P(OPh) 3] in refluxing 1,2-dichloroethane. Primary, secondary and tertiary benzyl acetates could be used for the reaction. Moreover, allylation of gem-benzyl acetate was possible with [Rh(cod)Cl]2, NaBARF, and P(OPh)3. Monoallylation and diallylation of gem-benzyl acetate could be controlled by altering the reaction conditions. Cationic rhodium species generated in situ act as a Lewis acid catalyst to give a benzyl carbocation by elimination of the acetoxy group from the benzylic carbon. Copyright
THE EFFECT OF THE POSITION OF THE DOUBLE BOND ON THE MECHANISM OF INTRAMOLECULAR CYCLOALKYLATION OF 2,4-DIMETHYL-4-PHENYLPENTENES IN SULFURIC ACID
Sakhabutdinov, A. G.,Usmanova, A. G.,Frolov, P. A.,Zinchenko, S. V.,Shmidt, F. K.
, p. 1043 - 1047 (2007/10/02)
Hydrogen exchange during the intramolecular cycloalkylation of 2,4-dimethyl-4-phenyylpentenes in 85percent sulfuric acid was studied by NMR and mass spectrometry. It was shown on the basis of the distribution of deuterium in 1,1,3,3-tetramethylindane that during cyclization of the endo-chain olefin the obtained γ-phenylalkyl cation undergoes partial deprotonation with the formation of an isomeric olefin whereas protonation of the terminal double bond is accompanied by rapid alkylation of the aromatic ring.
