Please use this identifier to cite or link to this item:
http://hdl.handle.net/11375/30069| Title: | MECHANISM OF DECOMPOSITION OF 5,5-DIARYL-N-NITROSO-2-OXAZOLIDONES |
| Authors: | VALENTIN, KAZIMER |
| Advisor: | Boums, A. N. |
| Department: | Chemistry |
| Keywords: | Chemistry |
| Publication Date: | May-1962 |
| Abstract: | A migration aptitude study has been made of the alkaline decomposition of 5,5-diaryl-N-nitroso-2-oxazolidone to diarylacetylene with the aim of shedding light on the mechanism of the rearrangement step of the reaction. 5-Phenyl-5-p-trifluoromethylphenyl-N-nitroso- 14 2-oxazolidone-5-C was synthesized and converted to p-trifluoromethyl- 14 tolane-C , which was oxidized to benzoic acid and p-trifluoromethylbenzoic acid. The ratio of specific activities of the two acids was found to be 1:2, showing that the migration tendency of the phenyl group is twice that of the p-trifluoromethylphenyl group. This result has been interpreted in terms of an electronically-controlled migration step involving as an intermediate either a vinyl carbonium ion or a vinyl carbene. |
| URI: | http://hdl.handle.net/11375/30069 |
| Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Valentin_Kazimir_1962May_masters.pdf | 3.65 MB | Adobe PDF | View/Open |
Items in MacSphere are protected by copyright, with all rights reserved, unless otherwise indicated.
