Selective C—H deuterium exchange in the oxacamphanyl moiety linked to the carbamide group

• Published in: Russian chemical bulletin Vol. 73; no. 7; pp. 1936 - 1943
• Main Authors: Nichugovskiy, A. I., Eshtukova-Shcheglova, E. A., Fayzullin, R. R., Kuznetsov, D. V., Burmistrov, V. V., Novakov, I. A.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.07.2024; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Deuterium; Full Articles; Inorganic Chemistry; NMR; Nuclear magnetic resonance; Organic Chemistry; camphanic acid; NMR; isocyanates; amines; crystal structure; ureas; deuterium exchange
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-024-4312-9

In the 1 H NMR spectra (DMSO-d 6 ) 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 2 —CH 2 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 3 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 2 —CH 2 group for a deuterium atom. This allows the selective modification of compounds containing the oxacamphanyl moiety.