Acetylenic and Polyacetylenic Compounds Derived from Thiophene, Furan, and p -Dibromobenzene Using 1,1-Dichloro-2,2-difluoroethene
1981; Oxford University Press; Volume: 54; Issue: 7 Linguagem: Inglês
10.1246/bcsj.54.2045
ISSN1348-0634
Autores Tópico(s)Catalytic Alkyne Reactions
ResumoAbstract Compounds of the type AZCF=CCl2, prepared from AZA (thiophene, furan, and p-dibromobenzene; Z=2,5-thiophenediyl, 2,5-furandiyl, and p-phenylene; A=H or Br), were converted into CCl2=CFZC≡CH, CCl2=CFZC≡CCF=CCl2, and CCl2=CFZC≡CSi(CH3)3 in a one-flask procedure via LiZC≡CLi. The products were further converted into acetylenic compounds such as (CH3)3SiC≡CZC≡CSi(CH3)3 and (CH3)3SiC≡CZC≡C–C≡CSi(CH3)3. 1-Ethynyl-4-(1,3-butadiynyl)benzene was isolated. 2,5-Diethynylthiophene and -furan were prepared in two steps from thiophene and furan, respectively, via CCl2=CFZCF=CCl2. By treatment with copper (II) acetate hydrate in pyridine, (CCl2=CFZC≡C–)2 were obtained not only from CCl2≡CFZC≡CH but also from CCl2=CFZC≡CSi(CH3)3.
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