59127-46-7Relevant academic research and scientific papers
Exploring the limitations of the MacDonald ‘3 + 1’ condensation in the preparation of porphyrins with fused electron-withdrawing heterocyclic rings: Synthesis of a bis(thiadiazolo)benzoporphyrin and a related benzocarbaporphyrin
Cillo, Catherine M.,Geiger, Mark A.,Lash, Timothy D.
, (2020)
A pyrrole ethyl ester with a fused bis(thiadiazolo)benzo unit was prepared by reacting 4-nitrobenzo[1,2-c:3,4-c’]bis(1,2,5)thiadiazole with ethyl isocyanoacetate in the presence of a non-nucleophilic base. Cleavage of the ester moiety, followed by reaction with a chloromethylpyrrole in refluxing pyridine, afforded a tripyrrane and subsequent acid-catalyzed condensation with pyrrole or indene dialdehydes gave porphyrinoids incorporating fused electron-deficient heterocyclic units.
MEHRFACH THIADIAZOL-UEBERBRUECKTE BENZOL- UND P-BENZOCHINON-RADIKALANIONEN UND IHRE Cr-, Mo- UND W-PENTACARBONYL-KOMPLEXE
Bock, Hans,Haenel, Peter,Neidlein, Richard
, p. 235 - 252 (2007/10/02)
Stable radical anions of bis(thiadiazolo)-p-benzoquinone as well as of bis- and tris(thiadiazolo)benzene derivatives form on one-electron reduction using potassium/ cryptand in THF solution.According to the assigned ESR spectra, their electron-rich sulfur centers exhibit especially large spin populations.On addition of THF soluble alkalimetal salts, the ESR signals vanish, whereas with metal hexacarbonyls Me(CO)6 paramagnetic mono- (Me = W) and di(metalpentacrbonyl) (Me = Cr, Mo, W) complexes result, for which HMO-McLachlan calculations suggest preferred coordination at the N centers of the same thiadiazol bridge.
