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Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom
Stereoselektivno slobodnoradikalsko fenilsulfenilovanje neaktiviranog δ-ugljenikovog atoma
dc.creator | Petrović, G. | |
dc.creator | Saičić, Radomir | |
dc.creator | Došen-Mićović, Ljiljana | |
dc.creator | Čeković, Živorad | |
dc.date.accessioned | 2018-11-22T00:07:29Z | |
dc.date.available | 2018-11-22T00:07:29Z | |
dc.date.issued | 2004 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/668 | |
dc.description.abstract | A stereoselective free radical introduction of a phenylthio group onto a nonactivated methyl group in the 8-position, adjacent to a prochiral carbon atom, was achieved by photolysis of (-)-menthyl benzenesulfenate in the presence of hexabutylditin and (1R, 3R, 4S, 8S)-9-phenylthiomenthot (4) was obtained with 91 % optical purity. High stereoselectivity of the reaction was calculated (ab initio MP2/6-3 1G**) to be the consequence of the difference in the transition state eneregies (DeltaDeltaG(#) = 5.08 kJ/mol) favouring 4 relative to (1R,3R,4S,8R)-9-phenylthiomenthoI (5). The absolute configuration of a the new chiral carbon atom was confirmed by its correlation with the corresponding menthane-3,9-diol of known stereochemistry. | en |
dc.description.abstract | Fotolizom (–)-mentil-benzensulfenata u prisustvu heksabutil-dikalaja izvršeno je stereoselektivno uvođenje feniltio grupe na neaktiviranu metil grupu u δ-položaju koja je susedna prohiralnom ugljenikovom atomu i dobiven je (1R 3R, 4S, 8S)-9-feniltio-mentol (4) sa 91 % optičke čistoće. Visoka stereoselektivnost reakcije, potvrđena računom (ab initio MP2/6-21G**) posledica je razlike u energijama prelaznih stanja ΔΔG# = 5.08 kJ/mol) koja favorizuje nastajanje 4 u odnosu na (1R, 3R, 4S, 8R)-9-feniltio-mentol (5). Apsolutna konfiguracija novog hiralnog ugljenikovog atoma potvrđena je korelacijom s odgovarajućim mentan-3,9-diolom poznate stereohemije. | sr |
dc.publisher | Serbian Chemical Soc, Belgrade | |
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 | radical reactions | en |
dc.subject | stereoselective reactions | en |
dc.subject | stereoselective reactions | en |
dc.subject | C-H activation | en |
dc.subject | C-H activation | en |
dc.subject | absolute configurations | en |
dc.subject | absolute configuration | en |
dc.subject | ab initio calculations | en |
dc.subject | ab initio calculations | en |
dc.subject | menthyl benzenesulfenate | en |
dc.subject | menthyl benzenesulfenate | en |
dc.subject | 9-phenylthiomenthol | en |
dc.subject | 9-phenylthiomenthol | en |
dc.title | Stereoselective free radical phenylsulfenylation of a nonactivated delta-carbon atom | en |
dc.title | Stereoselektivno slobodnoradikalsko fenilsulfenilovanje neaktiviranog δ-ugljenikovog atoma | sr |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Саичић, Радомир; Цековиц, З; Досен-Мицовиц, Л; Петровиц, Г; Стереоселективно слободнорадикалско фенилсулфениловање неактивираног δ-угљениковог атома; Стереоселективно слободнорадикалско фенилсулфениловање неактивираног δ-угљениковог атома; | |
dc.citation.volume | 69 | |
dc.citation.issue | 10 | |
dc.citation.spage | 737 | |
dc.citation.epage | 747 | |
dc.identifier.wos | 000224923100002 | |
dc.identifier.doi | 10.2298/JSC0410737P | |
dc.citation.other | 69(10): 737-747 | |
dc.citation.rank | M23 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-31544437728 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/9910/666.pdf |