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The dimesitylboron group in organic synthesis. 4. The ‘boron Wittig’ reaction

✍ Scribed by Andrew Pelter; Bakthan Singaram; John W. Wilson

Book ID
104216978
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
130 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

Anions generated c1-to a dimesitylboron group readily condense with aldehydes and ketones. reaction.

📜 SIMILAR VOLUMES

The dimesitylboron group in organic synt
The dimesitylboron group in organic synthesis 7. A unique variant of the Boron-Wittig reaction which stereoselectively yields 1,2-diols
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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.

The dimesitylboron group in organic synt
The dimesitylboron group in organic synthesis 1. Introduction.
✍ Andrew Pelter; Bakthan Singaram; Lorraine Williams; John W. Wilson 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 260 KB

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 synt
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✍ Manchak V. Garad; Andrew Pelter; B. Singaram; John W. Wilson 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 123 KB

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