13619-73-3Relevant articles and documents
Concentration and solvent effects on the conformational equilibrium of cis-3-ethoxycyclohexanol by 1H NMR and IR spectroscopy
de Oliveira, Paulo R.,Ortiz, Danilo S.,Rittner, Roberto
, p. 16 - 21 (2006)
NMR data, in CCl4, show that an increase in the concentration of cis-3-ethoxycyclohexanol (cis-3-ECH) shifts the conformational equilibrium from the ax-ax conformer (Xax-ax=51% at 0.01 mol L-1), stabilized by an intramolec
Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated ketones
Wu, Zhen,Feng, Xue-Xin,Wang, Qing-Dong,Yun, Jin-Jin,Rao, Weidong,Yang, Jin-Ming,Shen, Zhi-Liang
supporting information, p. 1297 - 1300 (2019/09/30)
An efficient method was developed for the conjugate addition of water to various α,β-unsaturated ketones by using bismuth(III) chloride as a catalyst. The reactions proceeded smoothly in the presence of a catalytic amount of BiCl3 (20 mol%) in aqueous media to furnish a variety of synthetically useful β-hydroxyl ketones in moderate to good yields. Apart from water molecule, various alcohols could also be employed as nucleophiles to react with α,β-unsaturated ketones, leading to β-alkoxyl ketones in modest to high yields. In addition, the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.
Chromium(III)-Catalyzed Addition of Water and Alcohol to α,β-Unsaturated Ketones for the Synthesis of β-Hydroxyl and β-Alkoxyl Ketones in Aqueous Media
Yun, Jin-Jin,Liu, Xuan-Yu,Deng, Wei,Chu, Xue-Qiang,Shen, Zhi-Liang,Loh, Teck-Peng
, p. 10898 - 10907 (2018/09/06)
An efficient chromium(III) chloride-catalyzed Michael-type reaction of water or alcohol with α,β-unsaturated ketones is developed. A variety of α,β-unsaturated ketones effectively reacted with either water or alcohols to give the corresponding β-hydroxyl ketones or β-alkoxyl ketones in modest to high yields with excellent compatibility to various functional groups. The approach was further utilized for the preparation of synthetically useful compounds containing tetrahydrofuran skeleton.
Catalytic behavior of melamine glyoxal resin towards consecutive oxidation and oxy-Michael addition
Ansari, Mohd Bismillah,Prasetyanto, Eko Adi,Lee, Jun,Park, Sang-Eon
scheme or table, p. 677 - 684 (2011/12/01)
Synthesis of melamine glyoxal resin involves a catalyst-free, one pot reaction between melamine and glyoxal in DMF. The synthesized resins have a similar morphological arrangement to that of layered materials as depicted by their XRD pattern and Raman spectra. The catalytic behavior of melamine glyoxal resin (MGR) have been studied in allylic oxidation of cyclohexene and simultaneous Michael addition. The MGR/solvent/O2 oxidant system can be regarded as a metalfree, additive-free, cost-effective and environmentally benign catalytic system. The oxidative behavior of MGR is attributed to its ability to generate in situ organic peroxide species during the course of reaction. Generation of peroxide species is confirmed by the KI/starch test and further confirmed by the complete suppression effect of TEMPO (2,2,6,6- tetramethylpiperidine-1-oxyl) over oxidation. The activity for Michael addition can be attributed to the presence of a higher content of nitrogen atoms, which serves as the active site. In oxidation, 28.1% conversion of cyclohexene with 37.19 and 62.81% selectivities for cyclohexenol and cyclohexenone were observed, respectively. In consecutive oxidation and oxy-Michael addition, 31.5% conversion of cyclohexene was observed with selectivities of 61.6% for cyclohexenone and 38.4% for alkoxy product. Springer Science+Business Media B.V. 2010.
