peri-NaphthylenediaminesUnexpected formation of naphtho[1,8-c,d]pyran derivatives in the reaction of 1,8-bis(dimethylamino)naphthalene with trifluoracetic anhydride. A new type of double naphthalene “proton sponges”

被引：0

作者：

A. F. Pozharskii

N. G. Tregub

N. V. Vistorobskii

E. Yu. Romanova

Z. A. Starikova

A. I. Yanovsky

机构：

[1] Rostov State University,A. N. Nesmeyanov Institute of Organoelement Compounds

[2] Russian Academy of Sciences,undefined

来源：

Russian Chemical Bulletin | 1999年 / 48卷

关键词：

1,8-bis(dimethylamino)naphthalene; “proton spronge”; naphthol[1,8-; ]pyran; - and; -diols; trifluoracetic anhydride; -acylation; covalent hydration; X-ray diffraction analysis; NMR spectra;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The reaction of 1,8-bis(dimethylamino)naphthalene (“proton sponge”) with trifluoroacetic anhydride afforded new derivatives of naphtho[1,8-c,d]pyran,viz., trans-) (4) andcis-1,3-dihydroxy-6,7-bis(dimethylamino)-1,3-bis(trifluoromethyl)-1H,3H-naphthol[1,8-c,d]pyran (5) and symmetrical 3,4,10,11-tetrakis(dimethylamino)-7,14-bis(trifluoromethyl)-7,14-epoxydinaphtho[1,8-a,b;1′, 8′-ef]cyclooctane (3), which belongs to a new type of double “proton sponges,” along with the expected 1,8-bis(dimethylamino)-4-trifluoroacetylnaphthalene. The structures of compounds3 and4 were established by spectral studies and X-ray diffraction analysis.

引用

页码：1299 / 1309

页数：10

共 26 条

[21] 1,8-Bis(dialkylamino)-4,5-dinitronaphthalenes and 4,5-Bis(dimethylamino)-naphthalene-1,8-dicarbaldehyde as "Push-Pull" Proton Sponges: When and Why Formyl Groups Become Stronger π-Electron Acceptors than Nitro Groups
Ozeryanskii, Valery A.
Pozharskii, Alexander F.
Artaryan, Alexander K.
Vistorobskii, Nikolai V.
Starikova, Zoya A.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (08) : 1241 - 1248
[22] The molecular structure of (PSH+)(nido-7,8-C2B9H12-) determined by neutron diffraction (PS = proton sponge, 1,8-bis(dimethylamino)naphthalene)
Fox, MA
Goeta, AE
Howard, JAK
Hughes, AK
Johnson, AL
Keen, DA
Wade, K
Wilson, CC
INORGANIC CHEMISTRY, 2001, 40 (01) : 173 - +
[23] COMPLEXES OF THE PROTON SPONGE 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE (DMAN) .7. THE OCCURRENCE OF A VERY SHORT ASYMMETRIC INTERMOLECULAR HYDROGEN-BOND IN THE 100-K STRUCTURE OF [DMANH]+.[D-HYDROGENTARTRATE]-.TRIHYDRATE
ISRAEL, OR
KANTERS, JA
GRECH, E
JOURNAL OF MOLECULAR STRUCTURE, 1992, 274 : 151 - 162
[24] Peri-naphthylenediamines .15. Transformations of 1,3-dimethylperimidone, 1,1,3-trimethyl-2,3-dihydroperimidinium and 1,8-bis(dimethylamino)naphthalene nitro derivatives under the action of alkali. Synthesis of N-methyl-substituted 1,8-diamino-4-nitronaphthalene and 8-amino-4-nitro-1-naphthol
Pozharskii, AF
Ozeryanskii, VA
Kuzmenko, VV
ZHURNAL ORGANICHESKOI KHIMII, 1996, 32 (01): : 76 - 82
[25] peri-Naphthylenediamines 32.: Reactions of 4,5-bis (dimethylamino)-1-naphthyllithium and 4,5-bis(dimethylamino)-1-naphthylmagnesium bromide with electrophilic agents.: New representatives of double naphthalene "proton sponges" with the structures of 1,1′-binaphthyl ketone and 1,1′-binaphthylmethanol
Ryabtsova, OV
Pozharskii, AF
Ozeryanskii, VA
Vistorobskii, NV
RUSSIAN CHEMICAL BULLETIN, 2001, 50 (05) : 854 - 859
[26] peri-Naphthylenediamines. 32. Reactions of 4,5-bis(dimethylamino)-1-naphthyllithium and 4,5-bis(dimethylamino)-1-naphthylmagnesium bromide with electrophilic agents. New representatives of double naphthalene “proton sponges” with the structures of 1,1"-binaphthyl ketone and 1,1"-binaphthylmethanol
O. V. Ryabtsova
A. F. Pozharskii
V. A. Ozeryanskii
N. V. Vistorobskii
Russian Chemical Bulletin, 2001, 50 : 854 - 859

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