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oai:gredos.usal.es:10366/1542422026-01-15T10:49:56Zcom_10366_4155com_10366_4055com_10366_3946com_10366_3823col_10366_4156

Titanocene-promoted stereoselective eliminations on epoxy alcohols derived from R-(−)-carvone Fernández Mateos, Alfonso Herrero Teijón, Pablo Rubio González, María Rosa Radical reactions Alcohols Titanium Elimination Esters 2306 Química Orgánica [EN]The reaction of several stereoisomeric epoxy alcohols, obtained from R-(−)-carvone, and their corresponding formates, acetates, and benzoates, promoted by Cp2TiCl has been studied. The different outcomes of the reaction of epoxy derivatives are rationalized in terms of mechanistically biased processes. The radicals emerging from oxirane cleavage provide two types of reaction: dehydroxylation (deoxycarbonylation) and dehydrogenation. The results offer considerable support for the radical elimination theory of hydroxyl, formyloxyl, and acetoxyl groups. The inability of tertiary radicals to be reduced by the Ti(III) complex is demonstrated unequivocally. 2024-01-15T11:57:57Z 2024-01-15T11:57:57Z 2013 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Fernández Mateos, A., Herrero Teijón, P. & Rubio González, R. (2013). Titanocene-promoted stereoselective eliminations on epoxy alcohols derived from R-(−)-carvone. Tetrahedron, 69(5), 1611–1616. https://doi.org/10.1016/j.tet.2012.11.093 0040-4020 http://hdl.handle.net/10366/154242 10.1016/j.tet.2012.11.093 eng https://doi.org/10.1016/j.tet.2012.11.093 Attribution-NonCommercial-NoDerivatives 4.0 Internacional http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess application/pdf https://gredos.usal.es/bitstream/10366/154242/5/2013%20Titanocene-promoted%20stereoselective%20eliminations%20on%20epoxy%20alcohols.pdf.jpg Hispana TEXT http://creativecommons.org/licenses/by-nc-nd/4.0/ Gredos. Repositorio Documental de la Universidad de Salamanca http://hdl.handle.net/10366/154242