ChemInform Abstract: Spontaneous Addition of Active Methine Compounds to Enol Ethers and α,β-Unsaturated Ketones in Aprotic Polar Solvent.

ChemInform ◽  
2010 ◽  
Vol 31 (27) ◽  
pp. no-no
Author(s):  
Tsutomu Yokozawa ◽  
Motoi Oishi ◽  
Yasukazu Tanaka
2021 ◽  
Vol 899 ◽  
pp. 337-341
Author(s):  
Diana H. Takova ◽  
Ludmila S. Lamashvili ◽  
Ludmila L. Dubovitskaya

Investigated the synthesis of polyphenylene sulfide in the environment of an aprotic polar solvent based on p-dichlorobenzene and p-dibromobenzene according to the nature comonomer rating. Infrared spectroscopy and thermogravimetric analysis of the obtained samples are presented.


2020 ◽  
Author(s):  
Yuji Naruse ◽  
Atsushi Takamori ◽  
Kenji Oda

For mechanism of decarboxylation reaction, all textbooks show that the electron moves from the pi<sub>C=O</sub> bond. However, the most donating bond orbital in the carbonyl group should be the lone pair(s) on the oxygen. Thus, a picture of orbital theory with delocalization from a lone pair should be more appropriate than that from the pi<sub>C=O</sub> orbital. We confirmed our idea by theoretical calculation. In the TS, if we use 2-substituted b-ketoacids, the boat-form conformation should result in exclusively preferred generation of <i>E</i>-enolates. Normally, decarboxylation reaction performs in polar solvent, so that the resulting enols should be transformed to the corresponding ketones by tautomerization. Suppose we use the heteroatoms to obtain the enolate or enol ethers without tautomerization, it would offer a diastereoselective enol(ate) synthesis with regioselectivity, since the C=C double bond should always be introduced between two carbonyl groups. After screening the heteroatoms by the theoretical calculations, we found that boron is suitable for this purpose. We confirmed our idea by theoretical calculations, offering a new boradecarboxylation reaction to produce enolates diastereoselecitively and regioselectively.


Sign in / Sign up

Export Citation Format

Share Document