Die Herz‐Reaktion beim 1.5‐Diaminonaphthalin

Benzo[1,2,3]dithiazole Compounds: A History of Synthesis and Their Renewed Applicability in Materials and Synthetic Chemistry, Originating from the Herz Reaction

“…It is interesting that the 5-membered dithiazole ring does not form as is known to happen with other naphthyl monoamines [16]. , alongside the dithiazoyl product that was not detected 12c [49].…”

“…Scheme 17. The product 12b obtained by Ried et al, alongside the dithiazoyl product that was not detected 12c [49]. In contrast to this example, a variety of aromatic compounds possessing two dithiazole moieties have been synthesised and characterised, although these have not been generated using the standard Herz reaction conditions [11,15].…”

“…The main issue is that the formation of one dithiazole ring likely deactivates the system to an additional S E Ar process. One of the earlier attempts to circumvent this was with 1,5-diaminonaphthalene [49], but the actual product isolated 12b was not the predicted compound 12c (Scheme 17). Instead, the proposed structure 12b was determined supported by the infrared spectra suggesting the presence of the thiosulfinic amide.…”

“…Scheme 17. The product 12b obtained by Ried et al, alongside the dithiazoyl product that was not detected 12c[49].…”