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1H and 13C NMR study of dihydro derivatives of methylphenobarbital

✍ Scribed by Marjatta Rautio; Erkki Rahkamaa

Publisher: John Wiley and Sons
Year: 1981
Tongue: English
Weight: 390 KB
Volume: 15
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270150112

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✦ Synopsis

Abstract

Sodium borohydride reduction of methylphenobarbital leads to the formation of two different dihydroderivatives, reduced either in position 4 or position 6. The structures of the derivatives have been determined through analysis of the ^1^H and ^13^C NMR spectra of phenobarbital, methylphenobarbital and their derivatives. Detailed interpretation of the spectra and the resulting spectral parameters indicate conformations where the hydroxyl groups are axial and trans to the ethyl group. In these configurations the phenyl ring becomes equatorial. The results also allow an unambiguous assignment of the resonances of the phenyl carbons 2′(6′) and 3′(5′) of phenobarbital and the carbonyl carbons 4 and 6 of methylphenobarbital, differing interpretations having been previously advanced in the literature.

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