A. I. Nichugovskiy, E. A. Eshtukova-Shcheglova, R. R. Fayzullin, D. V. Kuznetsov, V. V. Burmistrov, I. A. Novakov
{"title":"Selective C—H deuterium exchange in the oxacamphanyl moiety linked to the carbamide group","authors":"A. I. Nichugovskiy, E. A. Eshtukova-Shcheglova, R. R. Fayzullin, D. V. Kuznetsov, V. V. Burmistrov, I. A. Novakov","doi":"10.1007/s11172-024-4312-9","DOIUrl":null,"url":null,"abstract":"<div><p>In the <sup>1</sup>H NMR spectra (DMSO-d<sub>6</sub>) of 1,3-disubstituted ureas containing the 4,7,7-trimethyl-3-oxo-4-oxabicyclo[2.2.1]heptan-1-yl substituent, the signals for the CH<sub>2</sub>—CH<sub>2</sub> moiety appear as an ADMP-type spin system consisting of four doublets of doublets of doublets with chemical shifts in the range from 1.54 to 2.80 ppm. The experiment in CD<sub>3</sub>OD showed the disappearance of the signal at δ 2.80 and a change in the multiplicity of the other signals, which is indicative of the selective deuterium exchange of one of the four protons of the CH<sub>2</sub>—CH<sub>2</sub> group for a deuterium atom. This allows the selective modification of compounds containing the oxacamphanyl moiety.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1936 - 1943"},"PeriodicalIF":1.7000,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-024-4312-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
In the 1H NMR spectra (DMSO-d6) of 1,3-disubstituted ureas containing the 4,7,7-trimethyl-3-oxo-4-oxabicyclo[2.2.1]heptan-1-yl substituent, the signals for the CH2—CH2 moiety appear as an ADMP-type spin system consisting of four doublets of doublets of doublets with chemical shifts in the range from 1.54 to 2.80 ppm. The experiment in CD3OD showed the disappearance of the signal at δ 2.80 and a change in the multiplicity of the other signals, which is indicative of the selective deuterium exchange of one of the four protons of the CH2—CH2 group for a deuterium atom. This allows the selective modification of compounds containing the oxacamphanyl moiety.
期刊介绍：
Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections:
General and Inorganic Chemistry;
Physical Chemistry;
Organic Chemistry;
Organometallic Chemistry;
Chemistry of Natural Compounds and Bioorganic Chemistry.
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