89479-71-0Relevant academic research and scientific papers
Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity
Feng, Qiang,Huang, Hai,Sun, Jianwei
, p. 2431 - 2436 (2021/05/05)
Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect
Highly regioselective dipolar cycloadditions of nitrile oxides with α,β-acetylenic aldehydes
Jiang, Longqiang,Gao, Tao,Li, Zhi,Sun, Shaofa,Kim, Claudia,Huang, Changfeng,Guo, Haibing,Wang, Jian,Xing, Yalan
, p. 712 - 714 (2016/01/26)
1,2-Oxazol derivatives 3 were prepared by a highly regioselective 1,3-dipolar cycloaddition of nitrile oxides and α,β-acetylenicaldehydes 1 in good yields. Reactive nitrile oxides were generated in situ from stable chloro-oxime reagents 2 and triethyl ami
Cycloadditions of nitrile oxides to α,β-unsaturated aldehydes. Frontier orbital interactions and secondary orbital interactions at work in determining regiochemistry
Toma, Lucio,Quadrelli, Paolo,Perrini, Giancarlo,Gandolfi, Remo,Di Valentin, Cristiana,Corsaro, Antonino,Caramella, Pierluigi
, p. 4299 - 4309 (2007/10/03)
The regiochemistry of the cycloadditions of nitrile oxides to crotonaldehyde and cinnamaldehyde has been determined and is dictated by frontier orbital interactions and secondary orbital interactions as well. In cycloadditions to α,β-unsaturated compounds the directive effect of the frontier orbital interactions can be diverted by steric drifts and secondary orbital interactions. (C) 2000 Elsevier Science Ltd.
Nitrile Oxides Cycloadditions to Cinnamaldehyde. Facile Dehydrogention of 4-Formyl-4,5-dihydroisoxazoles
De Sarlo, Francesco,Guarna, Antonio,Brandi, Alberto
, p. 1505 - 1507 (2007/10/02)
Nitrile oxides (1) react with cinnamaldehyde (2) at the ethylenic double bond to give 4-formyl-4,5-dihydroisoxazoles (3) as the predominant regioisomers (1H nmr).These primary cycloadducts easily dehydrogenate to the corresponding isoxazoles (4).In the presence of an excess of nitrile oxide (1), either the aldehydes (3) and (4) undergo further cycloaddition at the C=O bond yielding the bis-cycloadducts (5) and (6), respectively.
