Highly conjugated architectures and labile reaction intermediates from coupling between 10π electron-deficient heteroaromatics andsym-trihydroxy- or triamino-benzene derivatives

Abstract

Novel intermediates of the SEAr/SNAr reaction (WM or M complexes) have been detected and characterized by NMR at low temperature.

Aryl diazonium salts and benzene derivatives bearing two electron-donor substituents: chemical and mechanistic behaviours

“…This implies that the obtained products are in salt form. A similar behaviour was reported in the literature in the reaction between tris-dialkylamino benzene derivatives and electrophiles such as benzofuroxan 19 and benzofurazan 18 derivatives. The only explanation for this is that the neutralization process might have occurred during the chromatographic purication, since this was the only work-up step to which the reactions were subjected.…”

“…This implies that the obtained products are in salt form. A similar behaviour was reported in the literature in the reaction between tris-dialkylamino benzene derivatives and electrophiles such as benzofuroxan 19 and benzofurazan 18 derivatives.…”

“…These compounds are able to react as carbon nucleophiles with a plethora of electrophiles such as, halogens, 1,2 protons, and [3][4][5][6][7][8][9][10][11][12] alkyl-, 13 acyl-, [14][15][16] and aryl-halides. [17][18][19] Moreover, the reaction of 1,3,5-tris(N,N-dialkylamino)benzenes with charged 20 and neutral carbon electrophiles has recently been studied, providing interesting information on the relevant reaction intermediates. [21][22][23] From long time our interest lies in the reaction between 1,3,5-tris(N,N-dialkylamino)-benzene derivatives and aryl diazonium salts from which it was possible to obtain evidence for the reversibility of the azo-coupling reaction and to detect the related Wheland-like reaction intermediates.…”

“…These compounds are able to react as carbon nucleophiles with a plethora of electrophiles such as, halogens, 1,2 protons, and 3–12 alkyl-, 13 acyl-, 14–16 and aryl-halides. 17–19…”

On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective Nucleophilic Substitution

“…The reactivity of some other chlorine or fluorine derivatives of 4,6-dinitrobenzofuroxan with some nitrogen, oxygen, and neutral carbon nucleophiles has also been examined. − …”