37622-98-3Relevant academic research and scientific papers
Multisubstituted phthalonitriles, naphthalenecicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanide syntheses
Leznoff, Clifford C.,Terekhov, Dmitri S.,McArtur, Colin R.,Vigh, Steven,Li, Jing
, p. 435 - 443 (2007/10/02)
Electrophilic aromatic nitration under mild conditions of 4-hydroxyphthalonitrile gave 4-hydroxy-3-nitrophthalonitrile and 4-hydroxy-5-nitrophthalonitrile, while bromination yielded 3-bromo-4-hydroxyphthalonitrile, 4-bromo-5-hydroxyphthalonitrile, and 3,5-dibromo-4-hydroxyphthalonitrile.Iodination gave 4-hydroxy-5-iodophthalonitrile and 4-hydroxy-3,5-diiodophthalonitrile.Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1,2-bis(tri-n-butylstannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-1,2-bis(2,3-dicyanophenyl) ethene, and trans-1,2-bis(6,7-dicyanonaphthyl)ethene.Photocyclization of a dilute solution of cis-or trans-1,2bis(3,4-dicyanophenyl)ethene in dioxane gave a 1:1 mixture of 2,3,6,7- and 2,3,5,6,-tetracyanophenanthrenes separable by chromatography.Key words: phthalonitriles, naphthalenedicarbonitriles, phenanthrenetetracarbonitriles, electrophilic substitution.
