Stereochemistry and mechanism of ionic cyclopropane ring cleavage by arenesulfenyl chloride addenda in quadricyclene systems

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dc.contributor.author Morrill, Terence en_US
dc.contributor.author Malasanta, Sumittada en_US
dc.contributor.author Warren, Karen en_US
dc.contributor.author Greenwald, Brian en_US
dc.date.accessioned 2006-07-19T18:42:46Z en_US
dc.date.available 2006-07-19T18:42:46Z en_US
dc.date.issued 1975-10-17 en_US
dc.identifier.citation The Journal of Organic Chemistry 40N21 (1975) 3032-3036 en_US
dc.identifier.issn 1520-6904 en_US
dc.identifier.uri http://hdl.handle.net/1850/2146 en_US
dc.description.abstract Addition of benzenesulfenyl chloride to quadricyclenedicarboxylic acid (la) and to the corresponding dimethyl ester (1b) gave adducts [exo-5-chloro-endo-3-phenylthiotricyclo[2.2.1.0^2,6]heptane-2,exo-3-dicarboxylic acid (3a) and the C-3 epimer (4a) from la and the corresponding dimethyl esters from lb, 3b:4b, ca. 1:1]; these are the result of electrophilic cleavage of a cyclopropane ring in this system by retention and inversion processes (in nearly equal amounts). The addition of toluenesulfenyl chloride to lb gives analogous results. All such results demonstrate the lack of bridged sulfonium ions (e.g., 2) as the sole product precursors and indicate that corner-attached electrophilic addition intermediates, relative to the corresponding edge-attached species, may have a far greater importance than previously suspected. The stereochemistry of the adducts was confirmed by spectral (largely proton magnetic resonance) and chemical (lactone formation) studies. en_US
dc.format.extent 31371 bytes en_US
dc.format.mimetype application/pdf en_US
dc.language.iso en_US en_US
dc.publisher The American Chemical Society: The Journal of Organic Chemistry en_US
dc.subject Adducts en_US
dc.subject Spectral and chemical studies en_US
dc.subject Stereochemistry en_US
dc.title Stereochemistry and mechanism of ionic cyclopropane ring cleavage by arenesulfenyl chloride addenda in quadricyclene systems en_US
dc.type Abstract en_US
dc.identifier.url http://dx.doi.org/10.1021/jo00909a006

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