Abstract
N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vinyl urea. Deprotonation of such a vinyl urea, or of an allyl urea, generates a dipole stabilized Z-allyl anion which may be protonated to return the Z-vinyl urea. Isomerization of an allyl urea with a Ru complex provides an alternative route to E-vinyl ureas.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemistry
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Amines / chemical synthesis*
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Amines / chemistry
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Combinatorial Chemistry Techniques
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Imines / chemistry
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Isocyanates / chemistry
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Molecular Structure
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Organometallic Compounds / chemistry
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Ruthenium / chemistry
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Stereoisomerism
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Urea* / analogs & derivatives
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Urea* / chemical synthesis
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Urea* / chemistry
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Vinyl Compounds / chemical synthesis*
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Vinyl Compounds / chemistry
Substances
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Amides
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Amines
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Imines
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Isocyanates
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Organometallic Compounds
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Vinyl Compounds
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Ruthenium
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Urea