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Please use this identifier to cite or link to this item: http://hdl.handle.net/1993/2917

Title: The complex photochemistry of 2,3-dibenzylidenesuccinates
Authors: Assoumatine, T
Yvon, B
Charlton, JL
Keywords: lignan
HINDERED 1,2-DIARYLIDENESUCCINIC ANHYDRIDES
APOPLICATITOXIN TRIMETHYL ETHER
OVERCROWDED MOLECULES
SYNTHETIC EXPERIMENTS
BETA-APOLIGNANS
PHOTOCYCLIZATION
STEREOCHEMISTRY
2,3-DIBENZYLIDENEBUTYROLACTONES
PHOTOREACTIONS
2,3-dibenzylidenesuccinate
Issue Date: 31-Aug-2000
Citation: 0008-4042; CAN J CHEM, AUG 2000, vol. 78, no. 5, p.553 to 561.
Abstract: The 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).
URI: http://hdl.handle.net/1993/2917
DOI: http://dx.doi.org/10.1139/v04-143
Appears in Collection(s):Research Publications (UofM Student, Faculty and Staff only access)

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