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

Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima

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2004
146.pdf (118.6Kb)
Authors
Krstić, Natalija
Bjelaković, Mira
Dabović, Milan
Lorenc, Ljubinka
Pavlović, Vladimir D.
Article (Published version)
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Abstract
Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) 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%).
Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.
Keywords:
(Z)-cholest-4-en-6-one oxime / 7-aza-B-homocholest-4-en-6-one / Beckmann rearrangement / photoreaction
Source:
Journal of the Serbian Chemical Society, 2004, 69, 6, 413-420
Publisher:
  • Serbian Chemical Society

DOI: 10.2298/JSC0406413K

ISSN: 0352-5139

WoS: 000222393300001

Scopus: 2-s2.0-4143050175
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/148
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