Origin of. alpha.-Hydroxy Ketones in the Osmium Tetroxide-Catalyzed Asymmetric Dihydroxylation of Alkenes

…, V Bhushan, R Krishna Kumar

Index: Lohray, Braj B.; Bhushan, Vidya; Kumar, R. Krishna Journal of Organic Chemistry, 1994 , vol. 59, # 6 p. 1375 - 1380

Full Text: HTML

Citation Number: 26

Abstract

Results Several olefins were dihydroxylated using TBHP as cooxidant and osmium tetroxide as catalyst. The results are summarized in Table 1. Large amount of a-hydroxy ketone is formed in each case. Thus, when trans-stilbene was oxidized with osmium tetroxide in the presence of aqueous TBHP in acetonitrile-water (4: l) at ca 0 OC, a mixture of benzoin (28%), hydrobenzoin (35%), and benzaldehyde (30%) were isolated (Table 1, entry 1). ...

Related Articles:

Butanones: Monoketones

[Lohray; Singh; Bhushan Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002 , vol. 41, # 6 p. 1226 - 1233]

Asymmetric Hydrosilylation of Ketones Using Trans-Chelating Chiral Peralkylbisphosphine Ligands Bearing Primary Alkyl Substituents on Phosphorus Atoms.

[Kuwano, Ryoichi; Sawamura, Masaya; Shirai, Junya; Takahashi, Masatoshi; Ito, Yoshihiko Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 2 p. 485 - 496]

Making mercury-photosensitized dehydrodimerization into an organic synthetic method. Vapor-pressure selectivity and the behavior of functionalized substrates

[Brown, Stephen H.; Crabtree, Robert H. Journal of the American Chemical Society, 1989 , vol. 111, # 8 p. 2935 - 2946]

The synthesis of glycols by mercury-photosensitized alcohol dehydrodimerization

[Lee, Jesse C.; Boojamra, Constantine G.; Crabtree, Robert H. Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 3895 - 3900]

Photochemical reaction of alcohols-I: Irradiation of aliphatic alcohols

[Balsells, R. Erra; Frasca, A. R. Tetrahedron, 1982 , vol. 38, # 2 p. 245 - 255]

More Articles...