825-24-1Relevant academic research and scientific papers
1-Bromo-1,2-dicyanoethylene: A dicyanoacetylene synthon useful in tetraazaporphyrin synthesis
Fitzgerald, Jeffrey P.,Korenak, John P.,Steinaker, Delano A.,Swogger, Logan M.,Lois, Jessica A.
, p. 1092 - 1099 (2019/09/20)
Dicyanoacetylene, a highly reactive dienophile, readily reacts to form substituted maleonitriles which serve as precursors to soluble tetraazaporphyrins. Unfortunately, dicyanoacetylene is difficult to synthesize in large quantities. We report here a new dicyanoacetylene synthon, 1-bromo-1,2-dicyanoethylene, which is easily made in high yield by reaction of elemental bromine with fumaronitrile and easily purified by vacuum distillation. The resulting 5:1 mixture of geometric isomers reacts with dienes via a Diels-Alder reaction followed by elimination of HBr to give substituted maleonitriles. We demonstrate the utility of these reactions by reporting the synthesis of a novel, soluble tetraazaporphyrin bearing four 1,4-fused cyclohexyl groups on the macrocycle periphery.
Reactions of bicycloalkenyldiiodonium salts with nucleophiles
Stang,Schwarz,Blume,Zhdankin
, p. 6759 - 6762 (2007/10/02)
Alkenyldiiodonium salts 1 react with a number of anionic nucleophiles to give the corresponding products of the vinylic nucleophilic substitution of the iodobenzene moiety. However, analogous reaction with Ph3P leads to the formation of tetraphenylphosphonium salt and diiodoalkene.
COBALT(II)TETRAPORPHYRIN-CATALYZED ISOMERISATION OF ELECTRONEGATIVE SUBSTITUTED QADRICYCLANES
Miki, Sadao,Ohno, Toshinobu,Iwasaki, Hideaki,Yoshida, Zen-ichi
, p. 3487 - 3490 (2007/10/02)
Co(II)TPP-catalyzed isomerisation of a series of electronegative substituted quadricyclanes(1) to the corresponding norbornadiene(2) was found to proceed via radicophilic attack of the metal to 1.
