167772-05-6Relevant academic research and scientific papers
One-pot synthesis of hypervalent diaryl(iodo)bismuthanes from o-carbonyl iodoarenes by zincation
Murafuji, Toshihiro,Hafizur Rahman,Magarifuchi, Daiki,Narita, Masahiro,Miyakawa, Isamu,Ishiguro, Katsuya,Kamijo, Shin
, (2019)
Diaryl(iodo)bismuthanes possessing a hypervalent C=O???Bi-I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds under mild reaction conditions that do not need low temperature control. Furthermore, no intermediate triarylbismuthane precursor for the hypervalent iodobismuthane is necessary.
Hypervalent bond formation in halogeno(2-acylphenyl)bismuthanes
Murafuji, Toshihiro,Mutoh, Takanori,Satoh, Kohichi,Tsunenari, Kazumi,Azuma, Nagao,Suzuki, Hitomi
, p. 3848 - 3854 (2008/10/09)
Hypervalent bond formation has been found to occur at bismuth as the hypervalent center. The transformation of (2-acetylphenyl)bis(4-methylphenyl)bismuthane (2b) to (2-acetylphenyl)bromo(4-methylphenyl)bismuthane (3b) brings about a noticeable change in the electronic nature of the carbonyl function in the 2-acetylphenyl group, which is sensitively reflected in the IR, 1H, and 13C NMR spectra of compound 3b. These spectral changes may be rationalized in terms of the formation of a hypervalent O-Bi-Br bond through intramolecular coordination of the carbonyl oxygen atom to the bismuth center. X-ray crystallography of 3b has confirmed this interpretation.
