Reaction of Phosphorus Ylides with Carbonyl Compounds in Supercritical Carbon Dioxide

Journal of the Korean Chemical Society

Choon Sup Ra¹  Hak Do Kim¹  Kyung Il Jeong¹  Jae-Jin Shim¹ 

关键词: Wittig ¹ÝÀÀ;    Supercritical;    Carbon dioxide;    Phosphoranes;    Phosphorus Ylides;    Wittig reaction;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 oC, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellant yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under scCO2 condition than in THF. The reaction of (benzylene)triphenylphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possibile tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.

【 授权许可】

Unknown