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EnglishThe acid induced ring opening of (R)-(+) styrene oxide (1R) or (S)-(−) styrene oxide (1S) is investigated in the gas phase, at a temperature of 25 °C and in the presence of a labeled nucleophile (CH318OH, CD3OH, or H218O). Various acid catalysts are generated in situ by γ radiolysis of the bulk gas (720 Torr of CH4 or CH3F). The mechanisms of the ring-opening reaction are assessed by modulating the composition of the gaseous mixture. Two reaction pathways are operative in the gas phase, both proceeding with the same regio- (100% at Cα) and stereochemistry (55–67% inversion of the Cα configuration). In the CH3F/H218O systems, a slow reaction takes place within a persistent proton-bound complex between the epoxide and the CH318OH2+ ion, formed by (CH3)2F+-methylation of H218O (the intracomplex pathway). When methanol is present in the gaseous mixtures, the intracomplex process is superseded by a faster extracomplex reaction, involving the attack of an external methanol molecule on the O-protonated epoxide. The present results are discussed in the light of related gas-phase and solution data.
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| Titolo: | Chiral Ions in the Gas Phase. 5. Acid-Induced Methanolysis of Optically Active Styrene Oxide. |
| Autori: | |
| Data di pubblicazione: | 1999 |
| Rivista: | |
| Handle: | http://hdl.handle.net/11573/45819 |
| Appartiene alla tipologia: | 01a Articolo in rivista |
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