PERI-NAPHTHYLENEDIAMINES - 25 - EVIDENCE FOR THE PARTICIPATION OF A RADICAL-CATION OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE (PROTON SPONGE) IN REACTIONS WITH NITRATING AGENTS - THE FORMATION OF 1,1'-BINAPHTHYL PROTON SPONGE AND THE REGIOSELECTIVE SYNTHESIS OF 4-CHLORO-1,8-BIS(DIMETHYLAMINO)NAPHTHALENE

Authors
OZERYANSKII VA POZHARSKII AF FOMCHENKOV AM
Citation
Va. Ozeryanskii et al., PERI-NAPHTHYLENEDIAMINES - 25 - EVIDENCE FOR THE PARTICIPATION OF A RADICAL-CATION OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE (PROTON SPONGE) IN REACTIONS WITH NITRATING AGENTS - THE FORMATION OF 1,1'-BINAPHTHYL PROTON SPONGE AND THE REGIOSELECTIVE SYNTHESIS OF 4-CHLORO-1,8-BIS(DIMETHYLAMINO)NAPHTHALENE, Russian chemical bulletin, 47(2), 1998, pp. 313-317
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
47
Issue
2
Year of publication
1998
Pages
313 - 317
Database
ISI
SICI code
1066-5285(1998)47:2<313:P-2-EF>2.0.ZU;2-8
Abstract
First indirect evidence for the formation of a radical cation of 1,8-b is(dimethylamino)naphthalene (''proton sponge'') in reactions with HNO 3, HNO2, NO2, and I-2 has been obtained. In all cases, the products of reaction of the radical cation with nucleophiles and/or its dimer, 4, 5,4',5'-tetrakis(dimethylamino)-1,1'-binaphthyl, have been isolated. 4 -Chloro-1,8-bis(dimethylamino)naphthalene has been regioselectively sy nthesized in high yield.