Acetylenic and polyacetylenic compounds derived from thiophene, furan, and p-dibromobenzene using 1,1-dichloro-2,2-difluoroethene.
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Compounds of the type AZCF=CCl<SUB>2</SUB>, prepared from AZA (thiophene, furan, and <I>p</I>-dibromobenzene; Z=2,5-thiophenediyl, 2,5-furandiyl, and <I>p</I>-phenylene; A=H or Br), were converted into CCl<SUB>2</SUB>=CFZC≡CH, CCl<SUB>2</SUB>=CFZC≡CCF=CCl<SUB>2</SUB>, and CCl<SUB>2</SUB>=CFZC≡CSi(CH<SUB>3</SUB>)<SUB>3</SUB> in a one-flask procedure <I>via</I> LiZC≡CLi. The products were further converted into acetylenic compounds such as (CH<SUB>3</SUB>)<SUB>3</SUB>SiC≡CZC≡CSi(CH<SUB>3</SUB>)<SUB>3</SUB> and (CH<SUB>3</SUB>)<SUB>3</SUB>SiC≡CZC≡C–C≡CSi(CH<SUB>3</SUB>)<SUB>3</SUB>. 1-Ethynyl-4-(1,3-butadiynyl)benzene was isolated. 2,5-Diethynylthiophene and -furan were prepared in two steps from thiophene and furan, respectively, <I>via</I> CCl<SUB>2</SUB>=CFZCF=CCl<SUB>2</SUB>. By treatment with copper (II) acetate hydrate in pyridine, (CCl<SUB>2</SUB>=CFZC≡C–)<SUB>2</SUB> were obtained not only from CCl<SUB>2</SUB>≡CFZC≡CH but also from CCl<SUB>2</SUB>=CFZC≡CSi(CH<SUB>3</SUB>)<SUB>3</SUB>.
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関連論文
- Acetylenic and polyacetylenic compounds derived from thiophene, furan, and p-dibromobenzene using 1,1-dichloro-2,2-difluoroethene.
- Preparation of fluorine-containing phenylacetylenes by the method of introduction of the ethynyl group using 1,1-dichloro-2,2-difluoroethene.