Reaction of 1,2,3-triphenylcyclopropene with free bromine in solvents of variable polarity
The three-membered ring of 1,2,3-triphenylcyclopropene is retained during radical bromination and is opened during electrophilic bromination, in which connection the character of the solvent determines either the radical or electrophilic mechanism of the reaction and the path of stabilizing the bromoallyl cation.
KeywordsBromine Variable Polarity Radical Bromination Free Bromine Electrophilic Mechanism
Unable to display preview. Download preview PDF.
- 1.G. A. Kudryavtseva and O. A. Nesmeyanova, Izv. Akad. Nauk SSSR, Ser. Khim., 2780 (1979).Google Scholar
- 2.R. F. Fawsett and J. C. Smith, Chem. Ind. (London), 871 (1960).Google Scholar
- 3.K. B. Wiberg and W. J. Bartley, J. Am. Chem. Soc.,82, 6375 (1960).Google Scholar
- 4.M. I. Komendantov, I. N. Domnin, R. M. Kenbaeva, and T. N. Grigor'eva, Zh. Org. Khim.,9, 1420 (1973).Google Scholar
- 5.L. Farnell and W. G. Richards, Chem. Commun., 334 (1973).Google Scholar
- 6.R. Breslow and H. W. Chang, J. Am. Chem. Soc.,77, 521 (1955).Google Scholar
- 7.R. Breslow and Chin Yuang, J. Am. Chem. Soc.,80, 599 (1958).Google Scholar