Keywords
(1R
3S)-3-acetyl-2,2-dimethylcyclobutane carboxylic acid
aprotonic solvents
mechanism of ozonolysis
ozonolysis of verbenone
Abstract
The ozonolysis of verbenone in methylene chloride and acetonitrile at –60 and 0°C proceeds with cleavage of the double bond and neighbouring σ-bond to give (1R,3S)-acetyl-2,2-dimethylcyclobutane carboxylic acid. The mechanism of the reaction has been proposed.
References
1.
10.1016/j.mencom.2009.03.019_bib1
Kukovinets
Khim. Prir. Soedin.,
2006
2.
10.1016/j.mencom.2009.03.019_bib2
Galin
Zh. Org. Khim.,
2001
3.
10.1016/j.mencom.2009.03.019_bib3
Kharisov
Zh. Org. Khim.,
2002
4.
10.1016/j.mencom.2009.03.019_bib4
Shereshovets
Neftekhimiya,
1980
5.
O. A. Reutov, A. L. Kurts and K. P. Butin, Organicheskaya Khimiya, BINOM, Moscow, 2004, vol. 3. (in Russian).
6.
10.1016/j.mencom.2009.03.019_bib6
Komissarova
Izv. Akad. Nauk SSSR, Ser. Khim.,
1978