Stereospecific formation of amidines by 1,1-addition of amines to isocyanides

Hegarty, A. F.; Chandler, Anne

doi:10.1016/s0040-4039(00)71534-6

Cited by 35 publications

(8 citation statements)

References 6 publications

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“…Both values are in the range expected for amidines (20,35). Although the geometry about the C=N bond cannot be determined from the spectroscopic data, amidines 20 were assigned the E geometry on the basis of the fact that amidines with the Z configuration are rare and are known to isomerize readily to the E form (35,36).…”

Section: Resultsmentioning

confidence: 99%

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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Treatment of 4-tert-butyl-3,3-dimethyl-5-methylene-Δ1-1,2,4-triazoline (3) with benzonitrile oxide (9), diphenylnitrile imine (10), phenyl azide, and p-nitrophenyl azide led, in each case, to 1,3-dipolar cycloaddition. The products, Δ1-1,2,4-tri-azolines that are spiro-fused to another 5-membered ring, could be isolated in pure form in three of the four cases. All four are thermally unstable and decompose by loss of N2 from the Δ1-1,2,4-triazoline moiety to form an azomethine ylide. Subsequent reactions of those ylides are described.

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Section: Resultsmentioning

confidence: 99%

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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“…Materials.-The ortho-substituted N ' N '-dimethyl-N2phenylformamidines (1)-- (6) were synthesized according to the procedure described in ref. 1 from dimethylformamide dimethyl acetal and the corresponding primary amines.…”

Section: Methodsmentioning

confidence: 99%

“…* The comparison indicates that the retention indices depend to a considerable degree on the position of the substituent in the phenyl ring. Moreover the retention index of the o-hydroxy derivative (6) is considerably lowered by intermolecular hydrogen-bond formation.…”

Section: E Zmentioning

confidence: 99%

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Retention indices and basicity of N¹N¹-dimethyl-N²-phenylformamidines. ortho-Substituent effect

Dolecka¹,

Raczyńska²,

Drapala³

1988

J. Chem. Soc., Perkin Trans. 2

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A series of ortho-substituted NIN1-dimethyl-N2-phenylformamidines (o-FDM P) have been synthesized and their structure determined by i.r. and 'H n.m.r. methods. All, except the hydroxy derivative, have the same structure ( E ) . In the case of the hydroxy derivative an intramolecular hydrogen bond appears, and thus two structures Z (20%) and E (80%) are observed in the 'H n.m.r. spectrum in CDCI,. The influence of the ortho-substituent on the retention indices, determined on a non-polar column, and on the pK, values, measured in 95.6% ethanol (azeotrope) and in water is discussed, and compared with those observed for meta-and para-derivatives. The retention indices of the ortho-derivatives, except the hydroxy derivative, obey the same linear correlation as meta-, para-, and other alkyl and aralkyl derivatives. A deviation of the pK, values of the ortho-derivatives from the linear correlations found for the meta-and para-derivatives are explained by steric effects of the substituent and medium effects.This paper reports the influence of ortho-substituents on the physicochemical properties of N ' N '-dimethyl-N ,-phenyl-

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“…The rearrangement is similar to the isomerization of vinylethyleneimine into pyrroline. The researchers suggested 28,29 that the reaction of aziridine with phenyl isocyanide gives rise to thermodynamically unstable Z-isomer 38, the transformation of which into the imidazoline 39 proceeds via initial Z,E-isomerization.…”

Section: Electrocyclic Reactionsmentioning

confidence: 99%

Heterocyclisation of trisubstituted formamidines containing an aryl or hetaryl substituent at the imine nitrogen atom

Oshovsky¹,

Пинчук²

2000

Russ. Chem. Rev.

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Stereospecific formation of amidines by 1,1-addition of amines to isocyanides

Cited by 35 publications

References 6 publications

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Retention indices and basicity of N¹N¹-dimethyl-N²-phenylformamidines. ortho-Substituent effect

Heterocyclisation of trisubstituted formamidines containing an aryl or hetaryl substituent at the imine nitrogen atom

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Stereospecific formation of amidines by 1,1-addition of amines to isocyanides

Cited by 35 publications

References 6 publications

The synthesis and unimolecular decomposition of four novel Δ1-1,2,4-triazolines

The synthesis and unimolecular decomposition of four novel Δ1-1,2,4-triazolines

Retention indices and basicity of N1N1-dimethyl-N2-phenylformamidines. ortho-Substituent effect

Heterocyclisation of trisubstituted formamidines containing an aryl or hetaryl substituent at the imine nitrogen atom

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The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Retention indices and basicity of N¹N¹-dimethyl-N²-phenylformamidines. ortho-Substituent effect