10522-02-8Relevant articles and documents
Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride
Ogawa, Haruo,Ide, Yuko,Honda, Ryoichi,Chihara, Teiji
, p. 355 - 358 (2003)
The selective acetylation of sterically hindered hydroxyl groups of 1,5-hexanediol preadsorbed on silica gel was reported. The relation between the adsorption of the diol on SiO2 and its reactivity for selective acetylation was studied. Results demonstrated that unsymmetrical diols get adsorbed on the surface of SiO2 preferentially via a primary OH group, leaving the non-adsorbed OH group available for reaction.
TiCl3(OTf) and TiO(TFA)2 efficient catalysts for ring opening of epoxides with alcohols, acetic acid and water
Iranpoor, Nasser,Zeynizadeh, Behzad
, p. 1017 - 1024 (1999)
TiCl3 (OTf) and TiO(TFA)2 can efficiently catalyze nucleophilic ring opening of epoxides in primary, secondary and tertiary alcohols, acetic acid and water to give the corresponding β-alkoxy alcohols, β-acetoxy alcohols and vicinal diols with high stereo- and regioselectivity in excellent yields. The reaction of optically active styrene oxide in MeOH with two titanium reagents was found to be highly stereospecific and afforded the corresponding S-(+)-2-methoxy-2-phenyl ethanol in 89-95% ee.
Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water
Lu, Yuchao,Wei, Peng,Pei, Yuxin,Xu, Hengfu,Xin, Xiaoting,Pei, Zhichao
, p. 4510 - 4514 (2014)
A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is
OXIDATION OF ISOXAZOLINES BY PERACIDS - A USEFUL ROUTE TO β-HYDROXY KETONES AND ACYLATED DIOLS
Park, Pyeong-uk,Kozikowski, Alan P.
, p. 6703 - 6706 (1988)
A method for bringing about the ring cleavage of isoxazolines by the use of peracids is described.
Synthesis and characterization of a novel Fe3O4@SiO2/bipyridinium dichloride nanocomposite and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azidoalcohols, β-cyanohydrins, and
Kiasat, Ali Reza,Chadorian, Fatemeh,Saghanezhad, Seyyed Jafar
, p. 1297 - 1306 (2015)
β-Azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols have been synthesized in the presence of a Fe3O4@SiO2/bipyridinium nanocomposite (Fe3O4@SiO2/BNC) as a novel magnetic and recyclable
Efficient and regioselective ring-opening of epoxides with carboxylic acid catalyzed by graphite oxide
Mirza-Aghayan, Maryam,Tavana, Mahdieh Molaee,Niazi, Elaheh Golam Alipour,Boukherroub, Rabah
, p. 532 - 538 (2020/07/17)
An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleo-phile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.
Aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) as a highly efficient and reusable catalyst for alcoholysis, hydrolysis, and acetolysis of epoxides
Tanemura, Kiyoshi,Suzuki, Tsuneo
, p. 1781 - 1789 (2016/11/17)
Alcoholysis, hydrolysis, and acetolysis of epoxides were carried out in the presence of a catalytic amount of aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) to give the corresponding β-substituted alcohols in good yields. Alcoholysis and hydrolysis of epoxides catalyzed by ATRT proceeded faster than those by pyridinium p-toluenesulfonate (PPTS).
