Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime | Zendy

Natalija M. Krstić | Zendy; Mira S. Bjelaković | Zendy; Milan Dabović | Zendy; Ljubinka Lorenc | Zendy; Vladimir B. Pavlović | Zendy

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Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime

Author(s) -

Natalija M. Krstić,

Mira S. Bjelaković,

Milan Dabović,

Ljubinka Lorenc,

Vladimir B. Pavlović

Publication year - 2004

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0406413k

Subject(s) - beckmann rearrangement , thionyl chloride , chemistry , isomerization , oxime , methanol , acetic acid , medicinal chemistry , yield (engineering) , ketone , benzene , lactam , chloride , organic chemistry , photochemistry , catalysis , materials science , metallurgy

Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3-ol1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e., 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7 %).

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