Journal article
Aralkylation of potassium ethylnitrosolate. Ring closure of nitrosolic acid esters
Journal of organic chemistry, Vol.41(18), pp.2985-2988
09/01/1976
DOI: 10.1021/jo00880a013
Abstract
The aralkylation of potassium ethylnitrosolate has been examined as a synthetic route to nitrosolic acid esters. The reaction of potassium ethylnitrosolate with representative benzylic halides did not stop at the ester stage but resulted in the formation of heterocyclic IV-oxides derived from the 1,2,4-oxadiazole ring system. The product was shown to be the N-4 rather than the N-2 oxide on the basis of NMR studies. A formal mechanism is proposed involving intramolecular reaction of the nitroso group of an intermediate nitrosolic acid ester with the benzylic methylene, followed by oxidation to the observed product. The sequence provides a new route to unsymmetrically substituted 1,2,4-oxadiazole 4-oxides. When the benzylic methylene is further substituted, as in the case of triphenylmethyl chloride, reaction with potassium ethylnitrosolate terminates at the corresponding ester. © 1976, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- Aralkylation of potassium ethylnitrosolate. Ring closure of nitrosolic acid esters
- Creators
- David F WiemerNelson J Leonard
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.41(18), pp.2985-2988
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00880a013
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 09/01/1976
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216587902771
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