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1.
5,6-Bis(dimethylamino)acenaphthylene is readily involved in [4+2] cycloaddition reactions with symm-tetrazine derivatives to form new proton sponges with the diazafluoranthene skeleton. Under analogous condition, 1,8-bis(dimethylamino)-4-vinylnaphthalene gave 4-pyridazinyl derivatives. The relative reactivities of 5,6-bis(dimethylamino)acenaphthylene, 1,8-bis(dimethylamino)-4-vinylnaphthalene, 5-dimethylaminoacenaphthylene, and acenaphthylene in the reactions with 3,6-diphenyl-symm-tetrazine are in a ratio of 32 : 17 : 14 : 1. The site of protonation of 3,4-bis(dimethylamino)-7,10-diphenyl-8,9-diazafluoranthene is controlled by the basicity of the solvent. The reaction in acetonitrile afforded the cation stabilized by an intramolecular hydrogen bond, whereas the reaction in dimethyl sulfoxide gave rise to the resonance-stabilized cation. 6,7-Bis(dimethylamino)phenalen-1-one was protonated only at the carbonyl group. 相似文献
2.
V. A. Ozeryanskii A. F. Pozharskii N. V. Vistorobskii 《Russian Chemical Bulletin》2000,49(7):1212-1217
o-Nitro ando,o′-dinitro derivatives of 1,8-bis(dimethylamino)naphthalene and its acenaphthene analog were prepared for the first time by
direct nitration with nitrogen dioxide or tetranitromethane. When 5,6-bis(dimethylamino)acenaphthene was treated with nitric
acid in AcOH or MeCN or with nitronium tetrafluoroborate in MeCN, nitration was accompanied by partial demethylation of one
of the NMe2 groups.
For Part 27, see Ref. 1.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1215–1220, July, 2000. 相似文献
3.
O. V. Ryabtsova A. F. Pozharskii V. A. Ozeryanskii N. V. Vistorobskii 《Russian Chemical Bulletin》2001,50(5):854-859
The 4-deuterio, 4-methyl, 4-iodo, 4-methylthio, 4-trimethylsilyl, and 4-ethoxycarbonyl derivatives of 1,8-bis(dimethylamino)naphthalene (proton sponge) and some related alcohols were prepared by the reactions of 4,5-bis(dimethylamino)-1-naphthyllithium or 4,5-bis(dimethylamino)-1-naphthylmagnesium bromide with the corresponding electrophilic reagents. New representatives of double proton sponges with the structures of 1,1"-binaphthyl ketone and 1,1"-binaphthylmethanol were synthesized. The pK
a values of selected compounds in DMSO were measured by competitive protonation. 相似文献
4.
A. F. Pozharskii O. V. Ryabtsova N. V. Vistorobskii Z. A. Starikova 《Russian Chemical Bulletin》2000,49(6):1097-1102
Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from
α-methyl-containing alcohols in an acidic medium underwent smooth El elimination to give the corresponding unsaturated derivatives
of the “proton sponge” in good yields. At the same time, the carbocation generated from 4-(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene
was converted into a benzo-[a]fluorene derivative as a result of a complex reaction which has been previously unknown in the chemistry of “proton sponges.”
The structure of the latter derivative was established by X-ray diffraction analysis.
For Part 26, see Ref. 1; this paper simultaneously presents Part 5 of the series “Resonance-stabilized α-naphthylmethyl carbocations
and derived spiro compounds;” for Part 4, see Ref. 2.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1103–1108, June, 2000. 相似文献
5.
4,5,4′,5′-Tetrakis(dimethylamino)-1,1′-binaphthalene, unknown previously, was obtained in ∼20% yield by the oxidation of 1,8-bis(dimethylamino)naphthalene
with Tl(OAc)3 or Pb(OAc)4 at low temperatures. Treatment of the reaction product with excess Li and then with O2 gave, depending on the reaction temperature, perylene or 4,4′-bis(dimethylamino)-1,1′-binaphthalene in good yields, instead
of expected 3,4,9,10-tetrakis(dimethyl-amino)perylene.
For Part 23, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 93–98, January, 1998. 相似文献
6.
A. F. Pozharskii N. G. Tregub N. V. Vistorobskii E. Yu. Romanova Z. A. Starikova A. I. Yanovsky 《Russian Chemical Bulletin》1999,48(7):1299-1309
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. 相似文献
7.
4-Hydroxymethyl derivatives of 1,8-bis(dimethylamino)- and 1,8-diiiiethoxynaphthalenes undergo cyclodirnerization on alumina to form symmetrical spir0, compounds of the head-to-tail type. The reaction is considered to be a two-step electrophilic substitution with the participation of naphthyhiiethyl carbocations.Translated fromIzvestiya Akademii Nauk, Seriya Khitnicheskaya, No. 4, pp, 1016–1018, April, 1996. 相似文献
8.
The action of concentrated HCl on 4,5-bis(diethylamino)-1-hydroxymethylnaphthalene resulted in its cyclodimerization of the
“head-to-head” type to form a spiro-compound, but, unlike its 4,5-bis(dimethylamino)-analog, cyclodimerization products did
not occur on Al2O3. The transformation of 4,5-bis(dimethylamino)-1-hydroxymethylnaphthalene on Al2O3, TiO2, and SiO2 afforded the previously unknown di[4,5-bis(dimethylamino)naphthyl-4]methane, a spiro-compound of the “head-to-tail” type.
4,5-Bis(diethylamino)-1-hydroxy-methylnaphthalene and 4,5-bis(diethylamino)naphthalene-1-carbaldehyde were synthesized.
For Part 18, see Ref. 1.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 348–350, February, 1997. 相似文献
9.
A. F. Pozharskii E. A. Filatova N. V. Vistorobskii I. V. Borovlev 《Chemistry of Heterocyclic Compounds》1999,35(3):319-327
Vilsmeier formylation of 1,3-dialkylperimidones, 1,3-dialkyl-2,3-dihydroperimidines, and 2-trifluoromethyl-perimidines is performed. The1H NMR spectra of the resulting mono- and dialdehydes are discussed.For No. 66, see [1].Rostov State University, Rostov-on-Don 344006Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 365–374, March, 1999. 相似文献
10.
The 1-[1,8-bis(dimethylamino)-4-naphthyl[ethyl carbocation generated from the corresponding alcohol in benzene in the presence of Al2O3 undergoes elimination according to theE1 mechanism to give previously unknown 1,8-bis(dimethylami no)-4-vinyl naphthalene in a good yield. This compound was also synthesized from 1,8-bis(dimethylamino)-4-formylnaphthalene by the Wittig reaction. Polymerization of the vinylic derivative obtained was studied.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2297–2300, September, 1996. 相似文献