The complex photochemistry of 2,3-dibenzylidenesuccinates

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dc.contributor.authorAssoumatine, T
dc.contributor.authorYvon, B
dc.contributor.authorCharlton, JL
dc.date.accessioned2007-10-09T18:53:04Z
dc.date.available2007-10-09T18:53:04Z
dc.date.issued2000-08-31
dc.description.abstractThe photochemistry of diethyl E,E-2,3-(3,4,5-trimethoxybenzylidene)succinate (8) is solvent dependent. In both protic and aprotic solvents, there is a photoequilibrium established between 8 and its E,Z-isomer (9). In chloroform at high light intensity, very little 9 is formed and the main product is 1,4-dihydronaphthalene (10), formed via photoinduced intramolecular [1,3]-sigmatropic hydrogen shift within an intermediate 1,8a-dihydronaphthalene (11). In protic solvents, irradiation of either 8 or 9 ultimately gives primarily the cis-1,2-dihydronaphthalene product (13), along with smaller amounts of the trans isomer (14). By using deuterated solvents, it was shown that 13 and 14 are formed by solvent protonation (or deuteration) of the 1,8a-dihydronaphthalene intermediate (11 or 12).en
dc.format.extent139856 bytes
dc.format.mimetypeapplication/pdf
dc.identifier.citation0008-4042; CAN J CHEM, AUG 2000, vol. 78, no. 5, p.553 to 561.en
dc.identifier.doihttp://dx.doi.org/10.1139/v04-143
dc.identifier.urihttp://hdl.handle.net/1993/2917
dc.language.isoengen_US
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dc.rightsopen accessen_US
dc.statusPeer revieweden
dc.subjectlignanen
dc.subjectHINDERED 1,2-DIARYLIDENESUCCINIC ANHYDRIDESen
dc.subjectAPOPLICATITOXIN TRIMETHYL ETHERen
dc.subjectOVERCROWDED MOLECULESen
dc.subjectSYNTHETIC EXPERIMENTSen
dc.subjectBETA-APOLIGNANSen
dc.subjectPHOTOCYCLIZATIONen
dc.subjectSTEREOCHEMISTRYen
dc.subject2,3-DIBENZYLIDENEBUTYROLACTONES
dc.subjectPHOTOREACTIONS
dc.subject2,3-dibenzylidenesuccinate
dc.titleThe complex photochemistry of 2,3-dibenzylidenesuccinatesen
dc.typejournal articleen_US
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