1416778-31-8Relevant articles and documents
Assembly of dimethyl acetylenedicarboxylate and phosphanes with aldehydes leading to γ-lactones bearing α-phosphorus ylides as wittig reagents
Deng, Jie-Cheng,Chan, Fu-Wei,Kuo, Chih-Wei,Cheng, Chun-An,Huang, Chien-Yu,Chuang, Shih-Ching
, p. 5738 - 5747 (2012/11/07)
We report herein a convenient route to the synthesis of aryl-substituted γ-lactones bearing an α-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl-or trialkylphosphanes in moderate to good yields. The formation of γ-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.