Naphthotriazine, I. Synthese <i>N</i>‐substituierter <i>peri</i>‐Naphthotriazine

Tavs, P.; Sieper, Helmut; Beecken, Hermann

doi:10.1002/jlac.19677040116

Cited by 24 publications

(6 citation statements)

References 8 publications

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“…It is well established that when the conjugate base of 1H-naphtho[1,8-de]-1,2,3,-triazine is alkylated with dimethyl sulfate a mixture of 1-and 2methylnaphtho[1,8-de]-1,2,3,-triazine, 2 and 3 results (Scheme 2). [18][19][20][21][22] Although the return of heterocycles from this methylation is good (70 %), the regioselectivity is poor and the mixture is close to 1:1 in the two isomers. The two isomers 2 and 3 are however readily separated and purified by column chromatography on silica gel.…”

Section: Resultsmentioning

confidence: 99%

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

et al. 2012

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By careful choice of reaction conditions 1‐methylnaphtho[1,8‐de]‐1,2,3‐triazine and 1,3‐dimethylnaphtho[1,8‐de]‐1,2,3‐triazinium triflate are readily prepared by the alkylation of 1H‐naphtho[1,8‐de]‐1,2,3‐triazine. The electronic spectra for these bathochromically shifted dyes are reported for a range of solvents as are their vibrational spectra and theoretical structures from density functional theory, B3LYP/6‐311++G**. The 15N substitution into the middle nitrogen atom allows for the identification of strong azine bands in the IR and Raman spectra as well as in the 15N NMR spectrum. X‐ray crystallography is used to characterize the solid‐state structures of two of these new triazine derivatives and these structures are used to benchmark the theoretical and spectroscopic discussions. The corresponding 1,3‐dimethyltriazinium radical is prepared and characterized by cyclic voltammetry, spectroelectrochemistry, and EPR spectroscopy. Unlike the related transient 1,2,4‐triazene radicals, the 1,3‐dimethyl‐1,2,3‐naphthotriazyl radical is markedly more stable.

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Section: Resultsmentioning

confidence: 99%

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

et al. 2012

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“…(3), which is obtained in 96.5 % yield from (2) While investigating the temperature dependence of formation of the benzene radical anion in T H F / D M E with liquid K/Na alloy, we observed that the ESR septet found at low temperatures (below about -2OOC) (Fig. 1) gives way on warming t o a new spectrum (Fig.…”

mentioning

confidence: 80%

A Novel Ring Fission of a 1,3‐Dimethyl‐1H‐naphtho[1,8‐de]‐1,2,3‐triazinium Salt

Beecken¹

1967

Angew. Chem. Int. Ed. Engl.

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“…It follows that (3) and (4) are formed from (2) by stepwise addition of electrons to the iron-phthalocyanine complex. If we include FePcC1, which has been described by Barrett et al [51, and whose structure as iron(111) phthalocyanine chloride we finally proved I61, we now know six iron-phthalocyanine complexes of differing total electron numbers.…”

Section: Bm [4]mentioning

confidence: 99%

“…), Amax (in methanol) = 503, 332, 318, 306, 227 m p with log E = 3.1 3, 3.86, 3.85, 3.77, 4.89. The structure of (3) follows from the bathochromic shift of the longest wavelength band in comparison with (2) Benzene radical anions, C6H6-, are obtained on reduction of benzene with alkali metals in solvent systems which dissolve the metals with formation of solvated electrons (e.g. tetra-…”

Section: Bm [4]mentioning

confidence: 99%

1‐Hexadecene, an Intermediate in the Microbial Oxidation of n‐Hexadecane in vivo and in vitro

Wagner

Zahn

Bühring

1967

Angew. Chem. Int. Ed. Engl.

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Only the first two reduction states have hirtherto been isolated, and closely studied, as crystalline lithium salts containing tetrahydrofuran, LitFePc1.4.5 THF ( I ) andLi2 [FePc].5.5 THF (2) 121. We have now obtained the third and the fourth reduction states in pure crystalline form.In order to prepare the third reduction state, pure recrystallized (2) in boiling THF was treated with a solution of dilithiobenzophenone in THF in the molar ratio 1 : 3. The third reduction state precipitates immediately. The dry compound forms darkolive-greencrystalsofcompositionLi~[FePcl~8THF ( 3 ) , which are very slightly soluble in THF but somewhat more soluble in dimethylformamide (DMF), to give intensely reddish-violet solutions.The fourth reduction state was obtained in the same manner, by treatment of (2) with dilithiostilbene, as violet crystals of composition Li4LFePcI-9 THF (4).The compound dissolves in THF to form an intensely bluish-green solution. It dissolves also in DMF but then rapidly decomposzs with development of a violet color. (3) and (4) are oxidized in air, with loss of tetrahydrofuran, (4) occasionally becoming incandescent. On oxidation of (3) and (4) with iodine in THF in the absence of air, 2.95 and 3.91 atoms, respectively, of iodine are consumed and [FePc] is formed. The electrolytic character of compounds (3) and (4) could be proved by transfer experiments in DMF or THF. Magnetic measurements by Gouy's method at temperatures between 83 and 293 OK substantiated the applicability of the Curie-Weiss law, xM = C / T + 8. Values found wereL31: for (3) : 8 = 35 "K, x (293 "K) = 1 . 4 4~ 10-6 cm3/g, g 2.60 B.M. [4] The saltsfor ( 4 ) : 0 = 12 "K, x (293 OK) = 3.08~ 10-6 cm3/g, ~'~f f =

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Naphthotriazine, I. Synthese N‐substituierter peri‐Naphthotriazine

Cited by 24 publications

References 8 publications

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

Permethylated Salts and Radicals Derived from Azo peri‐Naphthalenes

A Novel Ring Fission of a 1,3‐Dimethyl‐1H‐naphtho[1,8‐de]‐1,2,3‐triazinium Salt

1‐Hexadecene, an Intermediate in the Microbial Oxidation of n‐Hexadecane in vivo and in vitro

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