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Studies on the Reactivity of Cis-3-benzyloxy-1,2-epoxycyclohexane

AuthorsSabaté, Mar; Llebaria, Amadeu CSIC ORCID; Delgado Cirilo, Antonio
Nucleophilic attack
Base induced rearrangement
Issue Date2007
PublisherArkat USA
CitationARKIVOC: Online Journal of Organic Chemistry 2007(4): 188-195 (2007)
AbstractThe reaction course of the selenation-oxidation-elimination sequence carried out from cis-4-benzyloxy-1,2-epoxycyclohexane (cis-1) is studied. Contrary to literature precedents, this transformation leads to an unexpected diastereomeric cyclohexenol, whose formation can be interpreted by stereoelectronic grounds. In addition, the base induced rearrangement of cis-1 with lithium amide bases is also discussed. In the absence of external additives, a mixture of cyclohexenols arising from the competition of syn and anti elimination processes is observed. However, in the presence of Li salts, the corresponding cyclohexenol arising from an apparent anti elimination pathway predominates. A mechanistic rationale is proposed to account for these observations.
Description8 pages,5 schemes, 1 table.
Publisher version (URL)
ISSN1551-7004 (Online)
Appears in Collections:(IQAC) Artículos

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