The dimesitylboron group in organic synthesis 8. Preparations of 1,3-diols from oxiranes
โ Scribed by Andrew Pelter; Gina Bugden; Richard Rosser
- Book ID
- 104233304
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 222 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
Alkyldimesitylboranes, yield anions', by oxidation give 1,3-diols.
These anions
Mes2BCHR. that on reaction with oxiranes followed are thus the operational equivalent of RCHOH. The scope and limitations of the new process are delineated.
๐ SIMILAR VOLUMES
Low temperature oxidation of the intermediates in the Wittig reactions of aryl aldehydes with carbanions stabilised with an adjacent dimesitylboron group leads stereoselectively to erythro-1,2-diols. The mechanistic implications for the boron-Wittig reactions are discussed.
Dimesityl-3-hexylborane is unexpectedly resistant to isomerisation as compared with diphenyl-3-hexylborane. A possible explanation is proposed. Inorganic salts may profoundly affect the rate of isomerisation of diarylalkylboranes. \* We thank U.S. Racherla for informing us that 5% LiF, LiCl and LiBr