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The dimesitylboron group in organic synthesis 8. Preparations of 1,3-diols from oxiranes

โœ 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

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โœฆ 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.


๐Ÿ“œ SIMILAR VOLUMES


The dimesitylboron group in organic synt
โœ Andrew Pelter; Dieter Buss; Andrew Pitchford ๐Ÿ“‚ Article ๐Ÿ“… 1985 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 213 KB

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
โœ Andrew Pelter; Ashley Keating ๐Ÿ“‚ Article ๐Ÿ“… 1986 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 200 KB

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