Studies on the Chemistry of Heterocyclics. XV. The Synthesis of Thiophene Polyenes

Abstract

1. A series of cv, (,/-di-(2-thienyl) and -phenyl-w'-(2-thienyl) polyene hydrocarbons have been prepared.2. Several methods available for the synthesis of /3-cinnamalpropionic acid have been evaluated.3. The attempted preparation of thiophene polyenals is described.New York 58, N. Y.

Effect of Tetrahydroquinoline Dyes Structure on the Performance of Organic Dye-Sensitized Solar Cells

“…[1,2] 8a of E-configuration was prepared by McMurry coupling of 2-thiophenecarboxaldehyde. [3] 2,2,4-Trimethyl-1,2-dihydro-quinoline(1a)…”

“…[1,2] 8a of E-configuration was prepared by McMurry coupling of 2-thiophenecarboxaldehyde. [3] 2,2,4-Trimethyl-1,2-dihydro-quinoline(1a)To a solution of aniline (18.7 g, 0.2 mol) and toluenesulfonic acid (1.9 g) in cyclohexane (20 mL), acetone (42 mL, 0.57 mol) was added dropwise at 80~90 ºC for 8~10 h. The resulted water was removed by co-boiling with cyclohexane. Sodium carbonate (0.55 g) in water (20 mL) was poured into the reaction mixture after complete addition of acetone at 70 ºC.…”

Heterobenzyl quaternary ammonium salts. IV. 2-Thenyl group as terminus and migrating moiety in the Stevens and Sommelet rearrangements of a quaternary ammonium ion

“…1,2 -Di (2'-thienyl)ethylene (26). Salt 25 (0.4 mmol) in distilled water (4 ml) was heated with potassium hydroxide (1.5 g) at 110 °C for 60 min.…”

“…The identification of 26 was based upon its mass (M+ at m/e 192), 1H NMR, and ir (vai-C-H at 3020 cm-1, no yai-c=c due to trans isomerism, ¿oop 1-CH at 851,827, and 697 cm-1 for 2-substituted25 thiophene) spectra and its melting point. 26 The saturated compound 27 had physical properties (GLC and MS) identical with those of a sample prepared via a Wolff-Kishner reduction of the corresponding ketone with hydrazine and potassium hydroxide.5 A quaternary salt 28 could also be obtained from the Sommelet amine 14 with methyl iodide but 28 did not react with…”

“…The determination of rearrangement products was accomplished by separation and physical analysis, reactions of the material mixture to generate known compounds, and independent syntheses of predicted structures. This extended approach was essential because the rearranged products could salt upon treatment with hot aqueous potassium hydroxide gave l,2-di(2'-thienyl)ethylene (26) and when treated with lithium aluminum hydride l,2-di(2'-thienyl)ethane ( 27) together with 13 and 26. Reduction of 25 with sodium in liquid ammonia yielded 26 and 27.…”