15057-15-5Relevant academic research and scientific papers
A practical and scalable process to selectively monofunctionalize water-soluble α,ω-diols
Zhang, Quanxuan,Ren, Hong,Baker, Gregory L.
supporting information, p. 3384 - 3386 (2014/06/09)
A practical protocol for rapid and scalable synthesis of monofunctionalized α,ω-diols using a simple and inexpensive THP ether protection/deprotection strategy was described. Use of inexpensive DHP source and ease to remove excess water-soluble α,ω-diols
Selective monotetrahydropyranylation of symmetrical diols catalyzed by ion-exchange resins
Nishiguchi, Takeshi,Fujisaki, Shizuo,Kuroda, Masahumi,Kajisaki, Kohtaro,Saitoh, Masahiko
, p. 8183 - 8187 (2007/10/03)
Primary and secondary symmetrical diols with 2-10 carbon atoms gave selectively monotetrahydropyranyl ethers in the reaction catalyzed by wet sulfonic acid-type ion-exchange resins in 3,4-dihydro-2H-pyran (DHP)/toluene or DHP/hexane. The yields of the monoethers were higher than 80% while those of the corresponding diethers were lower than 5%. In these reactions the rate of the formation of the diethers did not increase much even after most of the diols had been consumed. In the reaction of 1,10-decanediol in DHP/hexane, the yields of the monoether were increased by the addition of DMF or DMSO. Each diol was found to have a particular DHP/hydrocarbon ratio that gave the highest selectivity for the monoether. Generally, the larger the number of carbon atoms of the diols, the smaller the ratio of DHP in the solvents to give high selectivity for the monoether. This method of the selective etherification is quite simple and practical.
Difunctionalized Trans-2,5-Disubstituted Pyrrolidine (Azethoxyl) Nitroxide Spin-Labels
Keana, John F. W.,Seyedrezai, Seyed E.,Gaughan, Glen
, p. 2644 - 2647 (2007/10/02)
The synthesis of two short-chain trans-2,5-difunctionalized azethoxyl nitroxide spin-labels, dinitrile 12 and dicarboxylic acid 14, is described.The trans stereochemistry of 12 and 14 was established by conversion of 12 to a diastereomeric mixture of N-hydroxy esters 13, which was analyzed by NMR spectroscopy.
