4,4-Bis(4-methylphenylsulfanyl)-1,1-diphenyl-2-azabuta-1,3-diene

Abstract

In the title compound, C29H25NS2, both the Cl atoms of the aza­diene precursor 4,4-dichloro-1,1-diphenyl-2-aza­buta-1,3-diene are replaced by two vicinal S-p-tolyl substituents attached to the terminal C atom of a π-conjugated 2-aza­butadiene array. The aza­diene chain is planar to within 0.01 Å. One of the phenyl rings seems to be slightly π-conjugated with the aza­diene core [dihedral angle 5.1 (2)°].

Crystal structure of 4,4-dibromo-1-(3,4-dimethoxyphenyl)-2-azabuta-1,3-diene-1-carbonitrile

“…In the context of our interest in developing novel -conjugated dithioether compounds as ligands for coordination chemistry and further organic transformations, we have reported on the synthesis and crystal structure of 4,4-dichloro-1,1-diphenyl-2-azabuta-1,3-diene [Ph 2 C N-C(H) CCl 2 ] and its conversion to [Ph 2 C N-C(H) C(SR) 2 ] and [Ph 2 C N-C(H) C(OPh) 2 ] by reaction with thiolates NaSR or NaOPh, respectively (Jacquot et al, 1999(Jacquot et al, , 2000Jacquot-Rousseau et al, 2006;Kinghat et al, 2016). Several crystal structures of these molecules/ligands and their derived transition metal complexes reveal that despite the overall planarity of the -conjugated chain, one aryl group of the -N CPh 2 imine segment is tilted with respect to the azabutadienic array (Jacquot et al, 1999;Knorr et al, 2003;Kinghat et al, 2008). To circumvent this feature and to modulate the stereoelectronic properties, we examined other synthetic strategies for the synthesis of 2-azabutadienes.…”

4,4-Bis(isopropylthio)-1,1-diphenyl-2-azabuta-1,3-diene Adducts with Cadmium(II), Mercury(II) and Copper(I) Iodides: Crystal, Molecular and Electronic Structures of d10 Transition Metal Chelate Complexes

“…In contrast to the plethora of 1,4-diazabutadien (α-diimine) complexes [1-3], 2-azabutadienes R 2 C=C(H)-N=CR ′ 2 (R, R ′ = Hal, alkyl, aryl) featuring a π-conjugated C=C(H)-N=C array are far less common as ligands in coordination chemistry [4]. We have developed an access to π-conjugated Cl 2 C=C(H)-N=CAr 2 via 1,3-dipolar cycloaddition and demonstrated that the chlorine atoms therein can be readily substituted with alcoholates, amides and thiolates [5][6][7][8][9]. The latter ditopic thioether-functionalized 2-azabutadienes (RS) 2 C=C(H)-N=CAr 2 in turn represent versatile ligands in coordination chemistry, since they dispose of both a harder imine-type N-donor site and a soft S-thioether site, allowing a chelating coordination on various transition metal centers.…”