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Synthesis 2001; 2001(1): 0093-0096
DOI: 10.1055/s-2001-9763
DOI: 10.1055/s-2001-9763
paper
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Direct Chlorovinylation and Ethynylation of Some C-H Acids Under Conditions of Phase Transfer Catalysis
Further Information
Publication History
Publication Date:
31 December 2001 (online)
Reactions of α-substituted phenylacetonitriles 1 with (E)-dichloromethylene (2) carried out in the presence of sodium or potassium hydroxide and tetra-n-butylammonium hydrogen sulfate (TBAHS) as a catalyst in cyclohexane-diethyl ether mixture (phase-transfer catalysis, PTC) gave (E)-2-chlorovinylated nitriles 3, usually in good yields. Liberation of the latent carbonyl group in 3f afforded (E)-2-chlorovinylphenylketone. On the other hand, 1,3-dialkylsubstituted indenes 4 reacted with (E)-dichloroethylene (2) under PTC conditions with formation of ethynylated indenes 5, in approx. 60-70% yield.
phase-transfer catalysis - chlorovinylation - ethynylation - nitriles - indenes