298. Amidines. Part XVI. A new synthesis of 1-alkyl- and 1-aryl-3 : 4-dihydroisoquinolines

Brodrick, C. I.; Short, W. F.

doi:10.1039/jr9510001343

Cited by 7 publications

(9 citation statements)

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“…The 19 Fa nd 31 PNMR spectra of 3a and 3b in CDCl 3 are nearly identical. Twor esonances (d( 19 F) = À36.9 and À67.6 ppm) are observed for the fluorine atoms bound to the phosphorus atom with coupling constants of 834 and 924 Hz.…”

Section: Resultsmentioning

confidence: 82%

“…This hydrogen bonding may be the reasonf or the doublet splitting of the NH proton with a J(FH) coupling constant of 25 Hz. Additionally,a 19 F, 1 HH OESY NMR experiment provesaclose proximity of the nuclei in solution.…”

Section: Resultsmentioning

confidence: 84%

“…The PÀNb ond lengths of 182.76 (19) pm resp. 183.52 (19) pm are about 8pms horter than in the 4-(dimethylamino)pyridine (DMAP)a dduct [P(C 2 F 5 ) 3 F 2 (dmap)] (190.9(1) pm).…”

Section: Resultsmentioning

confidence: 98%

“…The PÀNb ond lengths of 182.76 (19) pm resp. 183.52 (19) pm are about 8pms horter than in the 4-(dimethylamino)pyridine (DMAP)a dduct [P(C 2 F 5 ) 3 F 2 (dmap)] (190.9(1) pm). [8] The NÀC bonds are roughly equidistant( d av (NC) = 132.8 pm) and lie in the range of at ypical CN doubleb ond.…”

Section: Resultsmentioning

confidence: 98%

“…Neitherd oes it react with EtMgBr in diethyl ether or with methyl iodide. The reaction with nBuLi in hexane is sluggish:A fter 2days, small amounts of C 2 F 5 Ha nd C 2 F 4 are ob-served in the 19 FNMR spectrum.A fter stirring 1a for 5days in as olution of concentrated nitric acid in CH 2 Cl 2 ,t he 19 FNMR spectrum shows a3:1 mixture of 1a and [P(C 2 F 5 ) 3 F 3 ] À .C oncentrated sulfuric acid or methyl triflate selectively furnished (C 2 F 5 ) 3 PF 2 as ad ecomposition product according to a 19 FNMR spectrum of the mixture.…”

Section: Resultsmentioning

confidence: 99%

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Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines

Bader

Neumann

Stammler

et al. 2018

Chemistry A European J

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Acetonitrile is deprotonated by a combination of the strong Lewis acid (C F ) PF and triethylamine. The resulting cyanomethyl function is bound to the phosphorus moiety, affording the highly stable salt [HNEt ][P(C F ) F (CH CN)]. Salt metathesis reactions furnished the corresponding [Cu(MeCN) ] and [Ag(MeCN)] derivatives in which the CH CN substituent of the anion [P(C F ) F (CH CN)] coordinates to the metal. An investigation of the gas separation capability of the silver salt [Ag(MeCN)][P(C F ) F (CH CN)] shows an uptake of 1.7 equivalents of isobutene from a propane/isobutene mixture. The reaction of (C F ) PF with acetonitrile and diethylamine furnishes [P(C F ) F {NHC(CH )NEt }]-a phosphate featuring an amidine ligand which formally results from hydroamination of acetonitrile by HNEt . Exchange of HNEt with the primary amines H NPh and H NBu leads to comparable amidine salts that exhibit a solvent-dependent conformational isomerism.

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Section: Resultsmentioning

confidence: 82%

Section: Resultsmentioning

confidence: 84%

“…The PÀNb ond lengths of 182.76 (19) pm resp. 183.52 (19) pm are about 8pms horter than in the 4-(dimethylamino)pyridine (DMAP)a dduct [P(C 2 F 5 ) 3 F 2 (dmap)] (190.9(1) pm).…”

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines

Bader

Neumann

Stammler

et al. 2018

Chemistry A European J

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Pyridinecarboxylic Acids

Oliveto¹

1962

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Über einige Umsetzungen von Cyanstilbenderivaten

Knabe

Herbort

1967

Archiv der Pharmazie

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Bei der LiAlH,-Reduktion des Dicyanstilbens I b entsteht nicht IIb, sondern das Monaamin 111, das sich nach bekannten Verfahren in das Tetrahydroisochinolinderivat VI uberfiihren 1BBt. Das mit NaBH, aus I b erhaltene gesiittigte Dinitril VII liefert bei der Umsetzung mit LiAlH,/AICI, das cyclische Amidin VIII. Aus I b entsteht mit alkalischem H,O, das Epoxydiamid IS. Durch Hydrierung des Dicyanstilbens I a mit Raney-Nickel konriten Bretschneider und Lutzl) in geringer Ausbeute 1,4-Diamino-2,3-bis(4-methoxyphenyl)-butan (Ha) erhalten. Bei Versuchen zur Herstellung des fur Synthesezwecke benotigten analogen Tetramethoxyamins IIb aus Ib hatten wir keinen Erfolg. Uber das Ergebnis einiger Umsetzungen von I b sol1 im folgenden berichtet werden. R' &CN RidcN R a: R = OCH,; R' = H b: R = R ' = OCH, Die Synthese von I b gelingt nach Niederl und Ziering2) d u d oxydative Dimerisierung von 3,4-Dimethoxybenzylcyanid mit Jod und Natriummethylat.Bei dieser erstmals von Chalana y und Knoe~enagel~) angewandten Methode entstehen nach den Befunden von Niederl und Zieririg2) sowie von Bretschneider und Lutzl) cis-Stilbene, so daB wir auch I b-cis-Stilben-Konfiguration zuordnen miissen. Die Entscheidung, ob einem Stilben cis-oder trans-Konfiguration zukommt, laat sich normalerweise auf Grund seines UV-Spektrums treffen4) 5), da cis-Stilbene aus sterischen Griinden nieht koplanar gebaut seiii konnen. Bei a,cx'-Substitution biil3en jedoch auch trans-Stilbene ihre Koplanaritat ein, und eine Zuordnung nach dem UV-Spektrum ist nur dann moglich, wenn beide Isomere zur Verfugung stehen6).

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298. Amidines. Part XVI. A new synthesis of 1-alkyl- and 1-aryl-3 : 4-dihydroisoquinolines

Cited by 7 publications

References 0 publications

Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines

Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines

Pyridinecarboxylic Acids

Über einige Umsetzungen von Cyanstilbenderivaten

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298. Amidines. Part XVI. A new synthesis of 1-alkyl- and 1-aryl-3 : 4-dihydroisoquinolines

Cited by 7 publications

References 0 publications

Activation of Acetonitrile with (C2F5)3PF2 and Amines

Activation of Acetonitrile with (C2F5)3PF2 and Amines

Pyridinecarboxylic Acids

Über einige Umsetzungen von Cyanstilbenderivaten

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Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines

Activation of Acetonitrile with (C₂F₅)₃PF₂ and Amines