Welcome to LookChem.com Sign In|Join Free

Article Doi

First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts

DOI: 10.1039/p19960001971

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1971 - 1977 (1996)

Update date:2022-07-29

Topics:

Authors:

Matano, YoshihiroMatano, Yoshihiro

Yoshimune, MasanoriYoshimune, Masanori

Azuma, NagaoAzuma, Nagao

Suzuki, HitomiSuzuki, Hitomi

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/p19960001971

Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.

View More

Products guided by the article

Product name:(E)-2-(4-methylphenyl)ethenyl(triphenyl)bismuthonium tetrafluoroborate

Cas No:182330-12-7

182330-12-7

R&D Labs maybe for 182330-12-7

Relevant to this article

Hot Product