Stereocontrolled regiospecificity of the water loss from trans-sobrerol radical cation upon electron ionization
✍ Scribed by Antonio Selva; Francesco Ferrario; Paolo Ventura; Renato Pellegata
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- English
- Weight
- 531 KB
- Volume
- 22
- Category
- Article
- ISSN
- 1076-5174
No coin nor oath required. For personal study only.
✦ Synopsis
Water loss from trans-sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occurring by a stereocontrolled H-transfer from C(5) position in a rate-determining step process, as proved by '*O and deuterium labelling. Monomethyl ethers behave accordingly. Ionic structures of the water-loss product or products are investigated by metastable ion and collision activation mass-analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to trans-sobrerol in condensed phase, i.e. a-pinane epoxide, cis-sobrerol and pinol. A substantial conversion of cis-sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.