648416-48-2Relevant academic research and scientific papers
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.
The Aldol Reaction under High-Intensity Ultrasound: A Novel Approach to an Old Reaction
Cravotto, Giancarlo,Demetri, Alberto,Nano, Gian Mario,Palmisano, Giovanni,Penoni, Andrea,Tagliapietra, Silvia
, p. 4438 - 4444 (2007/10/03)
We have employed high-intensity ultrasound (HIU) to reinvestigate the aldol reaction (AR) in water. A number of aldols that under usual conditions would undergo elimination were isolated in acceptable to good yields. Within 15-30 min, acetophenone reacted with non-enolizable aldehydes to afford the aldol exclusively, while under conventional conditions (stirring or heating under reflux) the same compounds either failed to react or gave, after several hours, the enone, often in complex product mixtures. A library of polyols was obtained starting from a series of acetophenones and excess formaldehyde. Benzaldehyde reacted with a series of 1,3-dicarbonyl compounds to afford the corresponding bis(benzylidene) adducts. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
