caa a22 4500 465796087 CHVBK 20180323112038.0 cr unu---uuuuu 170327e19901201xx s 000 0 eng 10.1007/BF02541851 doi (NATIONALLICENCE)springer-10.1007/BF02541851 Organoselenium-mediated cyclization of hydroxyolefinic fatty acids and m-CPBA oxidation of selenium-containing 1,4-epoxy acids [Elektronische Daten] [R. Agarwal, A. Rauf, M. Khan, J. Mustafa, M. Ahmad] Chlorophenylselenenylation methodology is shown to cause cyclization of naturally occurring β- and γ-hydroxyolefinic acids. The phenylseleno-substituted 1,4-epoxides (tetrahydrofurans) thus obtained are oxidized by m-chloroperbenzoic acid (m-CPBA). Reaction of phenylselenenyl chloride with methyl 12-hydroxyoctadec-cis-9-enoate (methyl ricinoleate) gave methyl 9,12-epoxy-10-phenylselenenyloctadecanoate in useful yields. A similar reaction of phenylselenenyl chloride with methyl 9-hydroxyoctadec-cis-12-enoate afforded a quantitative yield of methyl 9,12-epoxy-13-phenylselenenyloctadecanoate. Oxidation of selenium-containing 1,4-epoxy esters by m-chloroperbenzoic acid (1 equivalent) yielded the respective olefinic 1,4-epoxy esters, while 5 equivalent m-CPBA afforded the corresponding oxirane esters of epoxytetrahydrofurans in high yields. The structure of the individual reaction products have been established from analytical and spectral data and corroborated by a study of their mass spectra. American Oil Chemists' Society (AOCS), 1990 Methyl ricinoleate nationallicence methyl isoricinoleate nationallicence oxirane 1,4-epoxide nationallicence phenylselenenyl chloride and 1,4-epoxides nationallicence Agarwal R. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut Rauf A. Applied Sciences, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut Khan M. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut Mustafa J. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut Ahmad M. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut Journal of the American Oil Chemists' Society Springer-Verlag 67/12(1990-12-01), 932-936 0003-021X 67:12<932 1990 67 11746 https://doi.org/10.1007/BF02541851 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02541851 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Agarwal R. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut NATIONALLICENCE 700 1- Rauf A. Applied Sciences, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut NATIONALLICENCE 700 1- Khan M. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut NATIONALLICENCE 700 1- Mustafa J. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut NATIONALLICENCE 700 1- Ahmad M. Section of Oils and Fats, Department of Chemistry, University Polytechnic, Faculty of Engineering and Technology, Aligarh Muslim University, 202 002, Aligarh, India aut NATIONALLICENCE 773 0- Journal of the American Oil Chemists' Society Springer-Verlag 67/12(1990-12-01), 932-936 0003-021X 67:12<932 1990 67 11746 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer