Tele-substitution reactions in the naphthalene series

Add time:07/24/2019    Source:sciencedirect.com

1,4 - Dimethyl - 2 - nitro - 3 - phenylsulphonylnaphthalene (2) reacts with sodium benzenethiolate in DMSO at 120° to give 1 - methyl - 2 - nitro - 4 - phenylthiomethylnaphthalene (4) [tele-substitution product (TSP) of the phenylsulphonyl group] and 1,4 - dimethyl - 3 - phenylsulphonyl - 2 - phenylthionaphthalene (5) [normal substitution product (NSP) of the nitro group]. The analogous reactions of 2 with sodium 2,4,6- trimethylbenzenethiolate and of 2,3 - bisphenylsulphonyl -1,4 - dimethylnaphthalene (3) with sodium benzenethiolate or aliphatic amines give only TSPs of the phenylsulphonyl group. In the case of the reaction of 2 with aliphatic amines both the possible TSPs (tele-substitution of the phenylsulphonyl or of the nitro group) were isolated in 9:1 relative yield. All the data show that the phenylsulphonyl is a leaving group far better than the nitro in such tele-substitution processes. The mechanism previously proposed to account for the formation of TSPs from 1,4-dimethyl - 2,3 - dinitronaphthalene is strongly supported by the obtained results.

We also recommend Trading Suppliers and Manufacturers of 1-(Phenylsulphonyl)-4-cyano-6-Methyl-7-azaindole (cas 1227270-24-7). Pls Click Website Link as below: cas 1227270-24-7 suppliers

Prev:Dienophilic reactivity of Trans-1,2-bis(phenylsulphonyl)ethylene: A valid alternative to maleic anhydride
Next:De Novo Synthesis of 3-Pyrrolin-2-Ones)