✦ LIBER ✦
The wittig reaction of non-stabilized phosphorus ylides and aromatic aldehydes. Studies on erythro and threo β-hydroxyphosphonium salts and the promotion of stereochemical drift by synergism between diastereomers
✍ Scribed by Bruce E. Maryanoff; Allen B. Reitz
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 293 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In deprotonation studies with isomerically pure ervthro-3 and m-3, "retro-Wittig" reaction was only detected for erythro-3. Mixtures of erythro-3 and threo-3. under -_ lithium salt-free conditions, undergo stereochemical drift because of synergism between diastereomeric oxaphosphetanes cis-2 and trans-2 during their decomposition to alkenes. -_ --Recently, we have observed' individual cis and trans oxaphosphetanes in the Wittig reaction of non-stabilized phosphorus ylides and aldehydes by 145.8~MHz 31P and 90.5MHz 13C NHR.2