The bulky dimesitylboron group encourages the formation of an o-carbanion from dimesitylalkylboranes by proton abstraction by a relatively hindered base, as compared with ate complex formation. It also stabilises the carbanion so formed. However the dimesitylboron group allows ate complex formation
The dimesitylboron group in organic synthesis 2. The c-alkylation of alkyldimesitylboranes
β Scribed by Andrew Pelter; Lorraine Williams; John W. Wilson
- Book ID
- 108381834
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 331 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
Anions generated c1-to a dimesitylboron group readily condense with aldehydes and ketones. reaction.
The synthesis of the title compounds where the heteroatoms are silicon, tin, lead and sulphur and mercury is demonstrated. Some of these derivatives readily form anions of structural and chemical interest. We have shown that carbanions stabilised by an c1 boron atom can be readily synthesised and a
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.
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