76331-08-3Relevant articles and documents
Photo-cleavage of carbon-carbon bond of α-iodocycloalkanones giving ω,ω-dialkoxyalkanoic ester in alcohol
Ji, Shun-Jun,Horiuchi, C. Akira
, p. 1645 - 1652 (2007/10/03)
The irradiation at λ > 300 nm of α-iodocycloalkanones with a high- pressure mercury lamp in alcohols containing a small amount of water afforded the corresponding ω,ω-dialkoxyalkanoic ester (65-88%) by photochemical cleavage of the C(I)-C=O bond at room temperature. In the case of a commercial fluorescent lamp as the irradiating light source, photochemical ring-opening products were also obtained. The irradiation of 2α-iodo-5α- and 4β-iodo-5β-cholestan-3-ones in methanol gave methyl 2,2-dimethoxy-2,3- seco-5α-cholestan-3-oate and methyl 4,4-dimethoxy-3,4-seco-5β-cholestan-3- oate in 78 and 62% yields, respectively. The photochemical behavior of the cleavage reaction of α-iodocycloalkanones is also discussed on the basis of 2-hydroxycycloalkanone as an intermediate.
ERZEUGUNG UND CYCLOADDITION VON ALLYLIUMIONEN AUS α-HALOGENKETONEN UNTER SOLVOLYSE-BEDINGUNGEN
Foehlisch, Baldur,Gottstein, Wolfgang,Kaiser, Roland,Wanner, Iris
, p. 3005 - 3009 (2007/10/02)
Some α-haloketones react with furan in methanolic solution in the presence of base to form the 3-oxo-8-oxabicyclooct-6-enes (11), the products derived from a cycloaddition of an allylium intermediate (5 or 6).