Y. Kato, T. Kuboyama, I. Hirao
Oct 1, 1972
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
In continuing a previous report concerning the syntheses and steric configurations of 3-(5-nitro-2-furyl)-2-(2-furyl)acrylic acid derivatives, trans and cis 3-(5-nitro-2-furyl)-2-(2-furyl)acrylonitrile and their related compounds have been synthesized. The isomerization was involved in the conversion of cis-3-(5-nitro-2-furyl)-2-(2-furyl)acrylamide (I) to trans-3-(5-nitro-2-furyl)-2-(2-furyl)acrylonitrile (II) upon the treatment of phosphoryl chloride. II was converted to its cis isomer (III) by treating it with hydroxylamine, hydrazine hydrate, or hydrochloric acid. II and III were treated with bromine at 5–10°C in carbon tetrachloride to afford dibromo compounds, (3S : 5S and 3R : 5R)-(IV) and (3S : 5R and 3R : 5S)-3-(5-nitro-2-furyl)-3-bromo-2-(5-bromo-2,5-dihydro-2-furylidene)propionitrile (V) respectively. When the bromination was carried out at a higher temperature (70–73°C), a monobromo compound, cis-3-(5-nitro-2-furyl)-2-(5-bromo-2-furyl)acrylonitrile (VI), was obtained from both II and III. VI wa...