DFT study on reaction mechanisms of propylamine and dimethyl acetylenedicarboxylate with 1,3-dimethylalloxan

2013 ◽  
Vol 1004 ◽  
pp. 47-55 ◽  
Author(s):  
Yanyan Zhu ◽  
Yunxia Li ◽  
Wenjing Zhang ◽  
Qilin Zhao ◽  
Mingsheng Tang
2018 ◽  
Vol 14 ◽  
pp. 2897-2906 ◽  
Author(s):  
Stanislav V Lozovskiy ◽  
Alexander Yu Ivanov ◽  
Olesya V Khoroshilova ◽  
Aleksander V Vasilyev

In strong Brønsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2–CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO–CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2–CR1=C–C(Me)=CH2, for R2 = R3 = Me, yields of 87–98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)–HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2–CR1=CH–C(OH)R2R3, yields of 78–99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-dioxides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2–CR1=CH–C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.


2014 ◽  
Vol 12 (33) ◽  
pp. 6374 ◽  
Author(s):  
Mengmeng Zhang ◽  
Donghui Wei ◽  
Yang Wang ◽  
Suiji Li ◽  
Jiefei Liu ◽  
...  

RSC Advances ◽  
2014 ◽  
Vol 4 (21) ◽  
pp. 10505 ◽  
Author(s):  
Hadieh Monajemi ◽  
Mun Hon Cheah ◽  
Vannajan Sanghiran Lee ◽  
Sharifuddin Mohd. Zain ◽  
Wan Ahmad Tajuddin Wan Abdullah

2005 ◽  
Vol 730 (1-3) ◽  
pp. 143-150 ◽  
Author(s):  
Li Guo ◽  
Zhong-Heng Yu ◽  
Shi-Zheng Zhu ◽  
Qing-Yun Chen

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