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The Riley oxidation is a selenium dioxide-mediated oxidation of methylene groups adjacent to carbonyls. It was first reported by Harry Lister Riley and co-workers in 1932. [ 1 ] In the decade that ensued, selenium -mediated oxidation rapidly expanded in use, and in 1939, Andre Guillemonat and co-workers disclosed the selenium dioxide-mediated ...
Organoselenium chemistry is the science exploring the properties and reactivity of organoselenium compounds, chemical compounds containing carbon-to-selenium chemical bonds. [ 1 ] [ 2 ] [ 3 ] Selenium belongs with oxygen and sulfur to the group 16 elements or chalcogens, and similarities in chemistry are to be expected.
The selenium starting material is reduced to selenium, and precipitates as a red amorphous solid which can easily be filtered off. [10] This type of reaction is called a Riley oxidation. It is also renowned as a reagent for allylic oxidation, [11] a reaction that entails the following conversion Allylic oxidation. This can be described more ...
The conversion of valencene to nootkatone is an example of allylic oxidation. In the synthesis of some fine chemicals, selenium dioxide is used to convert alkenes to allylic alcohols: [15] R 2 C=CR'-CHR" 2 + [O] → R 2 C=CR'-C(OH)R" 2. where R, R', R" may be alkyl or aryl substituents.
Selenium forms two oxides: selenium dioxide (SeO 2) and selenium trioxide (SeO 3). Selenium dioxide is formed by the reaction of elemental selenium with oxygen: [5] + It is a polymeric solid that forms monomeric SeO 2 molecules in the gas phase. It dissolves in water to form selenous acid, H 2 SeO 3.
Allyl alcohols in general are prepared by allylic oxidation of allyl compounds, using selenium dioxide or organic peroxides. Other methods include carbon-carbon bond-forming reactions such as the Prins reaction, the Morita-Baylis-Hillman reaction, or a variant of the Ramberg-Bäcklund reaction. Hydrogenation of enones is another route.
Riley remained at Imperial College as a demonstrator and later lecturer from 1923 to 1932, where he continued to pursue research in inorganic chemistry. He began to study the role of selenium oxides as oxidants of organic compounds, pioneering a new chemical process involving Selenium, known today as Riley oxidation. Whilst these studies ...
Selenium oxide may refer to either of the following compounds: Selenium dioxide, SeO 2; Selenium trioxide, SeO 3; Diselenium pentoxide, Se 2 O 5