
TY  - JOUR
A1  - Huppatz, JL 
A1  - Sasse, WHF 
T1  - Phenanthridines. IV. Pschorr reactions with sulphonamides derived from N-o-aminobenzylaniline: Synthesis of 4-bromophenanthridine and formationof 6-Phenyl-7H-dibenzo[d,f]-[1,2]-thiazepine-5-dioxide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1965
VL  - 18
IS  - 2
SP  - 206
EP  - 212
KW  - 
UR  - https://doi.org/10.1071/CH9650206 
N2  - The copper-catalysed decomposition of diazotized N-o-aminobenzyl-N-benzenesulphonylaniline (IIIb) yielded 5-benzenesulphonyl-5,6-dihydrophenanthri. dine (IIa) in lower yield than the Pschorr cyclization of N-benzenesulphonyl-N-benzyl-o-phenylenediamine (IIIa) previously studied. However, only one major by-product, 6-phenyl-7H-dibenzo[d,f]-[1,2]-thiazepine-5-dioxide (VIa) was formed from (IIIb). Pschorr cyclization of N-o-aminobenzyl-N-p-toluenesulphonyl-o-bromoaniline (IIIc) gave 4-bromophenanthridine (Ic) and 6-(2-bromophenyl)-2-methyl-7H-dibenzo[d,f]-[1,2]-thiazepine-5-dioxide (VIc). When this cyclization was carried out after diazotization with 30% excess sodium nitrite, N-benzyl-N-p-toluenesulphonyl-o-bromoaniline (IIIg) was also formed. 
ER  -

