PERI-NAPHTHYLENEDIAMINES .22. SYNTHESIS OF 1,4,5-TRIS(DIMETHYLAMINO)NAPHTHALENE AND OTHER PROTON SPONGE 4-AMINO DERIVATIVES

Authors
OZERYANSKII VA POZHARSKII AF
Citation
Va. Ozeryanskii et Af. Pozharskii, PERI-NAPHTHYLENEDIAMINES .22. SYNTHESIS OF 1,4,5-TRIS(DIMETHYLAMINO)NAPHTHALENE AND OTHER PROTON SPONGE 4-AMINO DERIVATIVES, Russian chemical bulletin, 46(8), 1997, pp. 1437-1440
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
46
Issue
8
Year of publication
1997
Pages
1437 - 1440
Database
ISI
SICI code
1066-5285(1997)46:8<1437:P.SO1>2.0.ZU;2-J
Abstract
Catalytic hydrogenation of 4-nitro-1,8-bis(dimethylamino)naphthalene a fforded the previously unknown 1-amino-4,5-bis(dimethylamino)naphthale ne subsequent methylation of which gave 1-methylamino and 1-dimethylam ino ''proton sponge'' derivatives. The pK(a) values of 1-amino-, 1-met hylamino-, and 1-dimethylamino-4,5-bis(dimethylamino)naphthalenes esti mated by H-1 NMR in DMSO-d(6) are equal to 9.8, 10.1, and 8.0, respect ively.