Transition metal-free one-pot reaction of quinolines with acylarylacetylenes and water proceeds in the presence of KOH (55-60 °C, MeCN, 48 h) to afford 2-aryl-3-acylquinolines in up to 66% yield. Here, a formal replacement of the acetylene moiety by the aryl and acyl substituents in the quinoline scaffold takes place. In fact, it has been proved experimentally that the reaction involves the ring cleavage, accompanied by the rearrangement and insertion of the electron-deficient acetylene moiety to form a dihydroquinoline intermediate with an aldehyde functional group in position 4. This intermediate gives the corresponding doubly functionalized quinolines.
Polyethylene exhaustively sulfurized with elemental sulfur shows paramagnetic (spin concentration 2.7--9.7" 1019 spg -1, g = 2.0041--2.0045, ~XH = 0.53--0.62 naT) and redox properties, which was demonstrated by both voltammetric and chemical methods (sodium reduction in liquid ammonia). The high concentration of unpaired electrons, the character of the electrochemical activity, and the chemical properties are in agreement with the presence in the polymers of polyconjugated ladder polythiophene and parquet polynaphthothienothiophene structures along with polyene-polysulfide blocks. The use of the polymers under consideration as an active cathode material in lithium batteries enables their repeated cycling with a specific charge capacitance of 150--340 mA h g-t.
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