par Wilputte, Roch 
;Martin, Richard
Référence Bulletin des Sociétés chimiques belges, 65, 9-10, page (874-898)
Publication Publié, 1956
;Martin, Richard Référence Bulletin des Sociétés chimiques belges, 65, 9-10, page (874-898)
Publication Publié, 1956
Article révisé par les pairs
| Résumé : | Fourteen (poly) benz‐9‐thiafluorenes are theoretically possible. This paper describes the synthesis of eight of them, namely: (1) 1,2,3,4‐dibenz‐9‐thiafluorene (m.p. 142°) (2) 1,2,6,7‐dibenz‐9‐thiafluorene (m. p. 317°) (3) 1,2,7,8‐dibenz‐9‐thiafluorene (m. p. 252‐253°) (4) 2,3,5,6‐dibenz‐9g‐thiafluorene (m. p. 197°) (5) 2,3,6,7‐dibenz‐9‐thiafluorene (m. p. 254°) (6) 1,2,3,4,5,6‐tribenz‐9‐thiafluorene (m. p. 196°) (7) 1,2,3,4,6,7‐tribenz‐9‐thiafluorene (m.p. 245°) (8) 1,2,3,4,5,6,7,8‐tetrabenz‐9‐thiafluorene (m. p. 259‐260°) (1,2,3,4,7,8‐tribenz‐9‐thiafluorene is the only (poly) benz‐9‐thiafluorene still unknown.) a) Compounds (1), (2), (4), (6) and (7) have been obtained according to the following scheme: 1° Condensation of an aromatic mercaptan with a cyclic α‐chloro ketone; 2° Cyclisation of the condensation product with P2O5 dehydrogenation (see tables II and III, p. 877 et 878). b) The polybenz‐9‐thiafluorenes (3) and (8) have been prepared by cyclodehydration of the corresponding diaryl sulfoxides by means of NaNH2. c) Reduction of 2,3,6,7‐dibenz‐9‐thiafluorene‐1,4,5,8‐diquinone (XXVIII p. 883) with Zn dust, NH4OH and NaOH gave compound (5). This same type of reduction applied to 4,9‐thiophanthraquinone (XXIX p. 8.3) provides a new and easy way to thiophanthrene. d) All the polybenz‐9‐thiafluorenes synthesised have been desulfurised with Raney Ni to the corresponding diaryls. e) This paper also describes the synthesis of thianaphthene‐4,5‐dicarboxylic anhydride (m. p. 172,5‐174°) (XXXIV p. 886) by standard methods. Copyright © 1956 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
