1178-00-3Relevant articles and documents
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Blunschy,Hardegger,Simon
, p. 199,203 (1946)
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Paranjape,Pyle
, p. 1009 (1971)
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Stiller,Rosenheim
, p. 353,355 (1938)
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Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage
Zhou, Zhong-Zhen,Liu, Mingxin,Lv, Leiyang,Li, Chao-Jun
supporting information, p. 2616 - 2620 (2018/02/13)
The oxidative cleavage of 1,2-diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H5IO6, Pb(OAc)4, and KMnO4, generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.
Autoxidation vs hydrolysis in 16α-acyloxy steroids
Slavikova, Barbora,Kasal, Alexander,Budesinsky, Milos
, p. 1125 - 1134 (2007/10/03)
Some enolizable α-hydroxy ketones are extremely susceptible to oxidation with traces of air in a reaction vessel. Autoxidation can be used in synthesis of oxo acids or diacids and their derivatives. Yet alkaline hydrolysis of the substrate is possible though under strictly air-free conditions.
Photoinduced Molecular Transformations. Part 106. The Formation of Cyclic Anhydrides via Regioselective β-Scission of Alkoxyl Radicals generated from 5- and 6-Membered α-Hydroxy Cyclic Ketones.
Suginome, Hiroshi,Satoh, Gen,Wang, Jian Bo,Yamada, Shinji,Kobayashi, Kazuhiro
, p. 1239 - 1245 (2007/10/02)
The irradiation of the hypoiodites of 5- or 6-membered cyclic α-ketols in benzene containing mercury(II) oxide and iodine (each 3 equiv.) resulted in the formation of the corresponding cyclic anhydrides arising from the insertion of an oxygen.A novel formation of a methylenedioxy group arising from an intramolecular hydrogen abstraction, on the other hand, was found when a steroidal α,α-dimethoxy alcohol hypoiodite was irradiated in benzene.An 18O labelling study of the formation of the cyclic anhydride on photolysis of 17β-hydroxy-4β-methoxy-5α-androstan-16-one hypoiodite generated in situ by an excess of mercury(II) oxide and iodine in benzene indicated that the heavy oxygen of Hg18O is incorporated as the ring oxygen of the anhydride.On the basis of this result, a pathway involving a regioselective β-scission of the alkoxyl radical is proposed as leading to formation of the cyclic anhydride.
