The dimesitylboron group in organic synthesis. 5. Hetero-atom substituted dimesitylborylmethanes.
β Scribed by Manchak V. Garad; Andrew Pelter; B. Singaram; John W. Wilson
- Book ID
- 104216979
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 123 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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 are of considerable synthetic utility.
π SIMILAR VOLUMES
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
Anions generated c1-to a dimesitylboron group readily condense with aldehydes and ketones. reaction.
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.