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 | |
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Valentin_Kazimir_1962May_masters.pdf | 3.65 MB | Adobe PDF | View/Open |
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