Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 10, Pages 4189-4193Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200522w
Keywords
-
Categories
Funding
- ETH Zurich
Ask authors/readers for more resources
A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by F-19 NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available