Synthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives

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dc.authoridYILMAZ, Ozgur -- 0000-0001-9278-1091; Simsek Kus, Nermin -- 0000-0002-5402-2614
dc.contributor.authorYılmaz, Özgür
dc.contributor.authorYıldız Bekfelavi, Esen
dc.contributor.authorŞimşek Kuş, Nermin
dc.contributor.authorTunç, Tuncay
dc.contributor.authorŞahin, Ertan
dc.date.accessioned13.07.201910:50:10
dc.date.accessioned2019-07-16T09:14:54Z
dc.date.available13.07.201910:50:10
dc.date.available2019-07-16T09:14:54Z
dc.date.issued2017
dc.departmentEğitim Fakültesi
dc.description.abstractThe addition of dichloroketene to 1,4-cyclohexadiene was examined. Dichloroketene, which was easily prepared from trichloroacetyl chloride and Zn-Cu, reacted with 1,4-cyclohexadiene in the presence of POCl3 to afford novel racemic products of single addition (5) and double addition (6). The adducts 6 and 7 were reacted separately with MCPBA (meta-chloroperbenzoic acid), H2O2, LiAlH4, and cis-diol 10 was reacted with PCC (pyridinium chlorochromate) to afford lactone, alcohol, and ketone derivatives likely to exhibit biological activity. The structures of all the racemic molecules mentioned in the article were determined from H-1 NMR, C-13 NMR, MS, and IR data.
dc.description.sponsorshipMersin University [BAP-FBE KA (OY) 2014-1DR, 2015-AP4-1235, BAP-FBE K (EYB) 2011-7 YL]; Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey [2010K120480]
dc.description.sponsorshipThe authors are indebted to Mersin University (BAP-FBE KA (OY) 2014-1DR, 2015-AP4-1235 and BAP-FBE K (EYB) 2011-7 YL) for its financial support of this work. The authors acknowledge Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 from the State Planning Organization).
dc.identifier.doi10.1007/s11696-016-0013-7
dc.identifier.endpage938en_US
dc.identifier.issn2585-7290
dc.identifier.issn1336-9075
dc.identifier.issue5en_US
dc.identifier.scopusqualityQ2
dc.identifier.startpage929en_US
dc.identifier.urihttps://doi.org/10.1007/s11696-016-0013-7
dc.identifier.urihttps://hdl.handle.net/20.500.12451/4206
dc.identifier.volume71en_US
dc.identifier.wosWOS:000400020200007
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer International Publishing Ag
dc.relation.ispartofChemical Papers
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/embargoedAccess
dc.subjectKetene Addition
dc.subjectTricyclic Molecules
dc.subjectLactone
dc.subjectKetone
dc.titleSynthesis of tricyclic ring systems: [2+2] ketene addition reaction for preparation of tricyclic ketone, alcohol, and lactone derivatives
dc.typeArticle

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