Cesium promoted O-alkylation of alcohols for the efficient ether synthesis
โ Scribed by Eric E. Dueno; Feixia Chu; Seok-In Kim; Kyung Woon Jung
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 256 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Efficient Williamson type O-alkylation of alcohols was developed using cesium bases in the presence of tetrabutylanmaonium iodide (TBAI) and molecular sieves. Various substrates including unreactive primary and secondary alcohols were converted smoothly to the corresponding ethers. Electrophiles used herein encompass primary bromides and reactive halides such as benzyl bromide and MPMCI.
๐ SIMILAR VOLUMES
The presence of cesium carbonate and tetrabutylammonium iodide (TBAI) facilitated efficient O-alkylation of alcohols with alkyl halides, giving rise to the exclusive formation of mixed alkyl carbonates, The cesium effect was also examined comparatively with other alkali carbonates.
Acetonyltriphenylphosphonium bromide (ATPB) is a precursor in the preparation of 1-(triphenylphosphoranylidene)-2-propanone used in a Wittig reaction. There are no reports on the use of ATPB in organic synthesis other than in ylide formation. 1 In the course of studying the counteranion effect on th