6222-18-0Relevant academic research and scientific papers
N-Heterocyclic Carbene-Catalyzed Chemoselective Monoacylation of 1, n-Linear Diols
Soeta, Takahiro,Kaneta, Kota,Hatanaka, Yuichi,Ida, Tomonori,Ukaji, Yutaka
supporting information, p. 8138 - 8142 (2021/11/01)
This paper discusses the N-heterocyclic carbene (NHC)-catalyzed redox monoacylation of 1,n-linear diols using α-benzoyloxyaldehydes. The reactions afforded monoacylated diols in moderate to good selectivities and chemical yields. Our original NHC bearing
Convenient Selective Monoacylation of 1,n-Diols Catalyzed by Ion-Exchange Resins
Nischiguchi, Takeshi,Fujisaki, Shizuo,Ishii, Yasuhiro,Yano, Yoshihiro,Nishida, Akiko
, p. 1191 - 1195 (2007/10/02)
Several 1,n-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were selectively monoacylated by transestrification in ester/octane solvent mixtures catalyzed by strongly acidic ion-exchange resisns.This method of selective esterification is quite simple and practical.The selectivity for monoester formation and initial rates of monoester formation depended on the ester/octane ratio of the solvents.The reasons for the selectivity are as follows: (1) The sulfonic acid-type ion-exchange resins usually contain 50-80percent water, and a strongly acidic aqueous layer is formed on the surface of the resins. (2) A partition equilibrium between the aqueous layer and the aprotic ester/octane layer is setup, and diols have higher partition coefficients than the product monoesters. (3) Acylation of the alcohols occurs in the aqueous layer and/or at the interface between the aqueous and the nonaqueous liquid layer. (4) The formed monoesters move away from the aqueous layer into the aprotic layer.
