The carbinyl acetylation shifts: A potential tool for differentiating the conformations of secondary allylic alcohols on six-membered rings
✍ Scribed by Takefumi Momose; Yutaka Ozaki
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- French
- Weight
- 249 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Acetylation shifts in iH-NMR spectroscopy have played an important role in organic chemistry since they were originally introduced, by Kawazoe and his coworkers, as a diagnosis for the relative spatial relationship between the ring methyls and hydroxyls in steroids and related compounds. 1 With regard to assignment of the hydroxyl conformation itself, however, their studies of carbinyl acetylation shifts terminated in ambiguous results. 2 Possible conformational dependency of the shifts for carbinyl protons mentioned by Tori and Komeno is not intended for practical use owing to the limited accumulation of data. 3 This paper describes a new practical method for determining the conformation of hydroxyls in tetralol analogs by use of acetylation shifts for benzylic carbinyl protons. 4