Abstract
Activated allylic compounds of the type RCH:CHCH(2)Z (Z = CN, CO(2)Me) react efficiently with aromatic aldehydes in the presence of 20-40 mol % of P(R'NCH(2)CH(2))(3)N at -94 to -63 degrees C. Both R = H and R = Me lead exclusively to alpha-addition products. When R = H and Z = CN, an allylic transposition occurs to afford a Baylis-Hillman product as the only product.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Aldehydes / chemical synthesis
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Aldehydes / chemistry
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Bridged-Ring Compounds / chemistry
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Catalysis
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Chemistry, Organic / methods
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Chromatography, Thin Layer
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Esters / chemistry
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Heterocyclic Compounds, 2-Ring / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Nitriles / chemical synthesis*
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Nitriles / chemistry*
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Organophosphorus Compounds / chemistry*
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Oxidation-Reduction
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Stereoisomerism
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Temperature
Substances
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Aldehydes
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Bridged-Ring Compounds
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Esters
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Heterocyclic Compounds, 2-Ring
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Nitriles
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Organophosphorus Compounds
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P(CH(3)NCH(2)CH(2))(3)N