Rearrangements in amidines and related compounds

Михайлов, И. Е.

doi:10.1002/9780470772478.ch11

PATAI'S Chemistry of Functional Groups

1991

DOI: 10.1002/9780470772478.ch11

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Rearrangements in amidines and related compounds

И. Е. Михайлов

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1992

2002

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Cited by 3 publications

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The Stabilization of Lithiated Organic Compounds by Water as a Ligand – Synthesis of a New Lithium–Imidazole Complex and Regioselective Reactions with Selected Electrophiles

Atzrodt

Beckert²,

Bräuer

et al. 1998

Eur. J. Org. Chem.

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The deprotonation of the 4H‐imidazoles 1 by lithium hydride yields the lithiated derivatives 2 which contain a stable delocalized anion. Surprisingly, the X‐ray crystal structure analysis of 2a reveals one molecule of water in the first complexation sphere of the lithium cation. This result is in good agreement with semiempirical calculations (PM3) which predict an increase in stability on substitution of ether ligands by water molecules. The deprotonation of 1 is accompanied by a change of colour from orange to purple because of the polymethinic character of the resulting anion. Alkylation, as well as acylation, of2 leads to the exocyclic substituted derivatives 3 and 5. The NMR spectra of 3 and 5 and the semiempirical calculations suggest the existence of two rotamers due to the low rotation barrier of the exocyclic C–N bond. Another type of acylation is observed when phenylacetyl chloride is used as an acylating agent. The X‐ray crystal structure analysis of 6c reveals that a rearrangement forming an unsaturated acid amide substructure takes place.

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The Stabilization of Lithiated Organic Compounds by Water as a Ligand – Synthesis of a New Lithium–Imidazole Complex and Regioselective Reactions with Selected Electrophiles

Atzrodt

Beckert²,

Bräuer

et al. 1998

Eur. J. Org. Chem.

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ChemInform Abstract: Rearrangements in Amidines and Related Compounds

Михайлов

1992

ChemInform

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A Novel Approach to [1,2,3]Triazolo[1,5-a]pyrazines

Vercek¹,

Jug²,

Polak³

et al. 2002

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Rearrangements in amidines and related compounds

Cited by 3 publications

References 151 publications

The Stabilization of Lithiated Organic Compounds by Water as a Ligand – Synthesis of a New Lithium–Imidazole Complex and Regioselective Reactions with Selected Electrophiles

The Stabilization of Lithiated Organic Compounds by Water as a Ligand – Synthesis of a New Lithium–Imidazole Complex and Regioselective Reactions with Selected Electrophiles

ChemInform Abstract: Rearrangements in Amidines and Related Compounds

A Novel Approach to [1,2,3]Triazolo[1,5-a]pyrazines

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