Retention of configuration at SP2 carbon in bimolecular nucleophilic displacement of halide ion from hydrazonyl halides

McCormack, Margaret T.; Hegarty, A. F.

doi:10.1016/s0040-4039(00)93741-9

Cited by 4 publications

(5 citation statements)

References 6 publications

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“…On the other hand, on addition of excess of Et4NCl to the reaction of lc or lg or addition of diisopropylammonium chloride to the reaction of lc with diisoprop-Ta-Shma, Rappoport / Mechanisms for Substitution of Diarylimidoyl Chlorides I04k', M-> s"> * k'/k°, " (iii) " The amine concentration used for the kinetic study. 6 The correlation coefficients of the linear plots of eq 2 are >0.995. c i k^obsd value at [amine] = 0. (see text).…”

Section: Resultsmentioning

confidence: 96%

“…From the linear log k\ vs. correlation of compounds ld-g a k\ value of (8.6 ± 0.5) 10~2 s_i was calculated for lc. By using this value and the slope and intercept of eq 12 we ob-Ta-Shma, Rappoport / Mechanisms for Substitution of Diarylimidoyl Chlorides 6 From EtOH. 1 (CDCh) 1.39 (12 H,d, Me), 3.68 (2 H, septet, CH), 7.05 (5 H, m, Ph), 6.37, 7.70 (4 H, AA'BB' q, C6H4Y) d Imidazolyl.…”

Section: Table VI and Figurementioning

confidence: 99%

See 1 more Smart Citation

Nucleophilic attacks on carbon-nitrogen double bonds. 3. Diversity of mechanisms for the substitution of diarylimidoyl chlorides by amines in acetonitrile

Ta‐Shma¹,

Rappoport²

1976

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 96%

Section: Table VI and Figurementioning

confidence: 99%

Nucleophilic attacks on carbon-nitrogen double bonds. 3. Diversity of mechanisms for the substitution of diarylimidoyl chlorides by amines in acetonitrile

Ta‐Shma¹,

Rappoport²

1976

J. Am. Chem. Soc.

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“…Methylation of adducts 9-11 with diazomethane occurs stereoselectively, affording (E)-1-methoxy-1-phenyl-2-azabuta-l,3-dienes [12][13][14].…”

Section: Resultsmentioning

confidence: 99%

“…There are several studies (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) on nucleophilic substitutions at the C-N double bond. A nucleophilic additionelimination mechanism or a pathway involving a nitrilium ion intermediate has been suggested.…”

Section: Methodsmentioning

confidence: 99%

2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

Lorente¹,

Casillas²,

Gomez-Sal³

et al. 1996

Can. J. Chem.

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Abstract:The synthesis of (E)-l-methoxy-2-azabuta-1,3-diene-4-carbonitriles was performed by methylation of Nalkenylamides 9 and 11. The Z isomers were obtained by treatment of (E)-I-methylthio-2-azabuta-I ,3-diene-4,4-dicarbonitriles with sodium methoxide in methanol. We also describe the reactions of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with pyrrolidine, which afforded 1-(1-pyrrolidinyl) derivatives 20,21, and 23. X-ray crystallographic analyses of 21 and 23 established the E stereochemistry of the C-N double bond. K~) Jwordr: 2-azabuta-l,3-diene-4-carbonitriles: stereoselective synthesis, nucleophilic substitution and X-ray diffraction; Nalkenylamides: methylation.Resume : On a effectui la synthkse des (E)-l-mithoxy-2-azabuta-1,3-di~ne-4-carbonitriles en effectuant la mithylation des Nalkinylamides 9 et 11. On a obtenu les isomkres Zen traitant les (0-1-mithylthio-2-azabuta-1,3-dikne-4,4-dicarbonitriles avec du mithylate de sodium dans le mithanol. On dicrit aussi les riactions des (E)-l-mithylthio-2-azabuta-I,3-dikne-4,4-dicarbonitriles avec la pyrrolidine qui conduisent aux dirivis 1-(I-pyrrolidinyle) 20,21 et 23. On a ditermini la stiriochimie E de la double liaison C-N par une analyse cristallographique par diffusion des rayons X.

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“…Moreover, it was reported that N,N-disubstituted hydrazonoyl halides 20 react with sodium methoxide in methanol to give the respective methyl hydrazonates 22 [23][24][25]. A kinetic study of methanolysis of (Z)-hydrazonoyl halides 20 9, Phenyl N-phenylbenzenecarbohydrazonoate, or ( Phenyl N-phenylbenzenecarbohydrazonate), with sodium methoxide indicated that such a reaction is stereospecific and follows a bimolecular mechanism to give the respective (Z)-hydrazonates [25].…”

Section: Methods Of Synthesis Of Hydrazonates 31 Synthesis Of Hydramentioning

confidence: 99%

The Chemistry of Hydrazonates

Shawali¹,

Sherif

2007

COC

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The chemistry of esters of hydrazonoic acids has gained increased interest in both synthetic organic chemistry and biological fields. Since a large number of developments in the use of such esters, a review of such developments, covering the literature up to mid 2005, seems to be of considerable value. The present review presents their structural features, nomenclature, synthetic methods and chemical reactions. The utility of the latter reactions for synthesis of various heterocyclic ring systems including mono-, bi-, tri-, tetra-, and penta-heterocycles. In addition, their silicon chelates and biological applications are presented.

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Retention of configuration at SP2 carbon in bimolecular nucleophilic displacement of halide ion from hydrazonyl halides

Cited by 4 publications

References 6 publications

Nucleophilic attacks on carbon-nitrogen double bonds. 3. Diversity of mechanisms for the substitution of diarylimidoyl chlorides by amines in acetonitrile

Nucleophilic attacks on carbon-nitrogen double bonds. 3. Diversity of mechanisms for the substitution of diarylimidoyl chlorides by amines in acetonitrile

2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

The Chemistry of Hydrazonates

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