127680-07-3Relevant academic research and scientific papers
Tandem [3+2] cycloaddition reaction of azo-alkenes and thiocyanic acid: Extending the scope of the classical "criss-cross" cycloaddition reaction
Schantl, Joachim G.,Nádeník, Peter
, p. 786 - 788 (2007/10/03)
Phenylazoalkenes 4 with full substitution at the terminal carbon atom react with thiocyanic acid affording 2,3,5,6,7,7a-hexahydro-3-phenyl-1H-imidazo[1,5-b][1,2,4]triazole-2,5-dithiones 8. The bicyclic compounds 8 result from two consecutive [3+2] cycloaddition steps, thus adding a novel facet to the classical "Criss-cross" reaction.
1-PHENYLAZO-1-ALKENES
Schantl, Joachim G.,Hebeisen, Paul
, p. 395 - 406 (2007/10/02)
Aliphatic aldehyde phenylhydrazones 1 were converted into 1-phenylazo-1-alkenes 3 either by the reaction with I2 and pyridine followed by base induced 1,4-elimination of pyridine.HI (Method A), or via N-(4-methylbenzenesulfonyl)-N-phenylhydrazones 7 which undergo 1,4-elimination of p-toluenesulfinic acid upon treatment with KOt-Bu (Method B).Both procedures yield mixtures of configurational isomers of the phenylazo-alkenes EE- and EZ- 3b-3e; Method B is giving rise to the kinetically controlled isomer mixture (EZ-3 predominant), which equilibrates to the thremodynamicratio (EE-3 predominant) as afforded by Method A.
