7399-32-8Relevant 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.
SYNTHESIS OF POLYCYCLIC ALKENES VIA REDUCTIVE ELIMINATION OF β-DICYANO DERIVATIVES: A FACILE PREPARATION OF ANTI-SESQUINORBORNENE AND RELATED MOLECULES
Lucchi, Ottorino De,Piccolrovazzi, Nicoletta,Modena, Giorgio
, p. 4347 - 4350 (2007/10/02)
Anti-Sesquinorbornene 1b, the hitherto unknown related unsaturated molecules 1a,c and the dienes 13 and 14 are among the endocyclic alkenes which can be prepared via reductive elimination of the respective, readily available β-dicyano derivatives.
