Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime
Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima
dc.creator | Krstić, Natalija | |
dc.creator | Bjelaković, Mira | |
dc.creator | Dabović, Milan | |
dc.creator | Lorenc, Ljubinka | |
dc.creator | Pavlović, Vladimir D. | |
dc.date.accessioned | 2019-01-30T17:12:07Z | |
dc.date.available | 2019-01-30T17:12:07Z | |
dc.date.issued | 2004 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/148 | |
dc.description.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%). | en |
dc.description.abstract | 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. | sr |
dc.publisher | Serbian Chemical Society | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | |
dc.subject | (Z)-cholest-4-en-6-one oxime | en |
dc.subject | 7-aza-B-homocholest-4-en-6-one | en |
dc.subject | Beckmann rearrangement | en |
dc.subject | photoreaction | en |
dc.title | Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime | en |
dc.title | Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Крстић, Наталија; Павловић, Владимир Д.; Дабовић, Милан М.; Бјелаковић, Мира; Лоренц, Љубинка Б.; Фотохемијско и Бекманово премештање(з)-холест-4-ен-6-он оксима; Фотохемијско и Бекманово премештање(з)-холест-4-ен-6-он оксима; | |
dc.citation.volume | 69 | |
dc.citation.issue | 6 | |
dc.citation.spage | 413 | |
dc.citation.epage | 420 | |
dc.citation.other | 69(6): 413-420 | |
dc.citation.rank | M23 | |
dc.identifier.doi | 10.2298/JSC0406413K | |
dc.identifier.fulltext | https://cer.ihtm.bg.ac.rs//bitstream/id/7945/146.pdf | |
dc.identifier.scopus | 2-s2.0-4143050175 | |
dc.identifier.wos | 000222393300001 | |
dc.type.version | publishedVersion |