Influence de la complexation sur la réactivité de nitrates d'halogènes

Gaude, Didier; Gellon, Gisèle; Goaller, R. Le; Pierre, Jean‐Louis

doi:10.1139/v89-018

Cited by 2 publications

(1 citation statement)

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“…Catalytic reduction of 3-nitrophthalonitrile (13) (21) with a poisoned palladium catalyst (22) gave 3-aminophthalonitrile (14) in 55-83% yields, which are considerably higher than previously reported (23). Diazotization of 14 and treatment of the diazonium salt with potassium iodide gave 3-iodophthalonitrile (IS), only mentioned in an article but not characterized (24).…”

Section: Bisdicyanoarylethenes From Dicyanoiodoarenesmentioning

confidence: 90%

Multisubstituted phthalonitriles, naphthalenedicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanine syntheses

Leznoff¹,

Terekhov²,

McArthur³

et al. 1995

Can. J. Chem.

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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-diidophthalonitrile. Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1.2-bis(tri-n-buty1stannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-I ,2-bis(2,3-dicyanophenyl)ethene, and trans-l,2-bis(6,7-dicyanonaphthy1)ethene. Photocyclization of a dilute solution of cis-or trans-I,2-bis(3,4-dicyanopheny1)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.Resume : La nitration Clectrophile aromatique du 4-hydroxyphtalonitrile, dans des conditions douces, conduit au 4-hydroxy-3-nitrophtalonitrile et au 4-hydroxy-5-nitrophtalonitrile alors que sa bromation fournit du 3-bromo-4-hydroxyphtalonitrile, du 4-bromo-5-hydroxyphtalonitrile, etdu3,5-dibromo-4-hydroxyphtalonitrile. L'iodation foumit du 4-hydroxy-5-iodophtalonitrile et du 4-hydroxy-3.5-diiodophtalonitrile. Le couplage des 4-iodophtalonitrile 3-iodophtalonitrile et 5-iodo-2,3-dicyanonaphtalkne avec du trans-l,2-bis(tri-11-butylstannyl)Cthkne fournit du trans-l,2-bis(3,4-dicyanophCnyl)6thkne, du trans-I ,2-bis(2,3-dicyanophCny1)Cthkne et du trans-1.2-bis(6,7-dicyanonaphty1)Cthkne. La photocyclisation d'une solution diluCe des isomkres cis-et trans-l,2-bis(3,4-dicyanophCny1)tthkne dans le dioxane fournit un melange I : 1 des 2,3,6.7-et 2.3.5.6-tCtracyanophCnanthrknes que l'on peut separer par chromatographie.

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Section: Bisdicyanoarylethenes From Dicyanoiodoarenesmentioning

confidence: 90%