1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP): a powerful condensing reagent for phosphate and phosphonate esters

TETRAHEDRON

卷:62

Article

Oka, N ; Shimizu, M ; Saigo, K ; Wada, T

关键词: phosphonium-type condensing reagent;    phosphate;    alkylphosphonate;    boranophosphate;    H-phosphonate;   

DOI  :  10.1016/j.tet.2006.01.084

来源: Elsevier

【 摘 要 】

A novel phosphonium-type condensing reagent, 1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP), was designed and synthesized. A P-31 NMR study oil the condensation reactions of phosphate, alkylphosphonate , boranophosphate, and H-phosphonate derivatives with an alcohol in the presence of MNTP demonstrated the versatility and the enhanced activity of the new condensing reagent, compared to the previously reported phosphonium-type condensing reagents. The mechanism of the condensation reactions mediated by MNTP is discussed on the basis of the P-31 NMR studies and theoretical calculations. (c) 2006 Elsevier Ltd. All rights, reserved.

【 授权许可】

Free