Direct Chlorovinylation and Ethynylation of Some C-H Acids Under Conditions of Phase Transfer Catalysis

Andrzej Joczyk; Agnieszka H. Gierczak

doi:10.1055/s-2001-9763

Synthesis 2001; 2001(1): 0093-0096
DOI: 10.1055/s-2001-9763

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Direct Chlorovinylation and Ethynylation of Some C-H Acids Under Conditions of Phase Transfer Catalysis

Andrzej Jończyk^* , Agnieszka H. Gierczak

^*Warsaw University of Technology, Faculty of Chemistry, Koszykowa 75, 00-662 Warsaw, Poland; Fax +48(22)6 28 27 41; E-mail: anjon@ch.pw.edu.pl

Abstract

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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

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