57668-32-3Relevant academic research and scientific papers
Photoisomerization of Trans Ortho-, Meta-, Para-Nitro Diarylbutadienes: A Case of Regioselectivity
Agnihotri, Harsha,Paramasivam, Mahalingavelar,Palakollu, Veerabhadraiah,Kanvah, Sriram
, p. 1324 - 1331 (2015/11/10)
A series of ortho-, meta- and para-substituted trans-nitro aryl (phenyl and pyridyl) butadienes have been synthesized and characterized. The effect of substitution and positional selectivity on their fluorescence and photoisomerization were systematically investigated. Among all dienes, meta- and para-nitro phenyl-substituted derivatives exhibit remarkable solvatochromic emission shifts due to intramolecular charge transfer. On the other hand, ortho derivatives undergo regioselective isomerization upon photoexcitation in contrast to inefficient isomerization of para and meta nitro-substituted dienes. Single crystal X-ray analysis revealed existence of intramolecular hydrogen bonding between the nitro group and the hydrogen of the proximal double bond. This restricts the rotation of the proximal double bond thereby allowing regioselective isomerization. The observations were also supported by NMR spectroscopic studies.
Synthesis and evaluation of a series of 1,4-diarylbutadienes for anticoccidial activity
Gage, Jennifer L.,Kirst, Herbert A.,O'Neil, Deirdre,David, Bridget A.,Smith II, Charles K.,Naylor, Sharon A.
, p. 4083 - 4091 (2007/10/03)
During the course of a collaborative screening program, a set of 1-phenyl-4-pyridyl-butadienes was found to exhibit in vitro activity against Eimeria tenella in a cell-based assay. Activity was dependent on the chain length and degree of unsaturation of t
A NOVEL SYNTHESIS OF (E,E)-1,4-DIARYL-1,3-BUTADIENES BY THE RUTHENIUM(II) CATALYZED REACTION OF (E)-2-ARYLETHENESULFONYL CHLORIDES WITH VINYLARENES
Kamigata, Nobumasa,Ozaki, Jun-ichi,Kobayashi, Michio
, p. 705 - 708 (2007/10/02)
Symmetrical and unsymmetrical (E,E)-1,4-diaryl-1,3-butadienes can be prepared in high yields from (E)-2-arylethenesulfonyl chlorides by treating with vinylarenes in the presence of ruthenium(II) phosphine complex in benzene.
Reaction of Alkenesulfonyl Chlorides with Olefins Catalyzed by a Ruthenium(II) Complex. A Novel Method for Synthesis of (E,E)-1,4-Diaryl-1,3-butadienes
Kamigata, Nobumasa,Ozaki, Jun-ichi,Kobayashi, Michio
, p. 5045 - 5050 (2007/10/02)
In the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II) (1), alkenesulfonyl chloride (2) was found to react with vinylarenes to give 1:1 adducts (3) in high yield under mild conditions.Dehydrochlorination from the adducts 3 to afford divinyl sulfones (4) takes place by raising the reaction temperature from 80 to 130 deg C.Upon further reaction at 150 deg C, (E,E)-1,4-diaryl-1,3-butadienes (5) are formed in high yield if both of the alkenyl substituents of the sulfonyl chloride and the alkene have aryl groups.The time course of the reaction indicates that the addition of 2 to vinylarenes giving 1:1 adducts 3, dehydrochlorination from the adducts 3 giving divinyl sulfones 4, and desulfonylation from the divinyl sulfone 4 giving 1,3-butadienes 5 proceed successively.The usefulness of the reaction for the syntheses of (E,E)-1,4-diaryl-1,3-butadiene is described.On the other hand, 2 reacts with alkyl olefins in the presence of 1 to give 1:1 adducts (12) with extrusion of sulfur dioxide.
