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dc.contributor.author Assoumatine, T
dc.contributor.author Yvon, B
dc.contributor.author Charlton, JL
dc.date.accessioned 2007-10-09T18:53:04Z
dc.date.available 2007-10-09T18:53:04Z
dc.date.issued 2000-08-31
dc.identifier.citation 0008-4042; CAN J CHEM, AUG 2000, vol. 78, no. 5, p.553 to 561. en
dc.identifier.uri http://hdl.handle.net/1993/2917
dc.description.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). en
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dc.format.mimetype application/pdf
dc.language.iso en_US
dc.rights No part of the NRC Research Press electronic journals may be reproduced, stored, or transmitted in any form or by any means, without the written permission of the publisher, except as stated below. Under the Canadian Copyright Act, individuals may download or print single copies of articles for personal research or study. Any person may reproduce short excerpts from articles in the journals for any purpose that respects the moral rights of authors, provided that the source is fully acknowledged. As a courtesy, the consent of authors of such material should be obtained directly from the author. Authorization to reproduce items for other than personal research or study, as stated above, may be obtained via Access © upon payment of the copyright fee of $10.00 per copy. NRC Research Press also extends certain additional rights to authors. The above rights do not extend to copying or reproduction for general distribution, for advertising or promotional purposes, for creating new collective works, or for resale. For such copying or reproduction, arrangements must be made with NRC Research Press. en
dc.rights info:eu-repo/semantics/openAccess
dc.subject lignan en
dc.subject HINDERED 1,2-DIARYLIDENESUCCINIC ANHYDRIDES en
dc.subject APOPLICATITOXIN TRIMETHYL ETHER en
dc.subject OVERCROWDED MOLECULES en
dc.subject SYNTHETIC EXPERIMENTS en
dc.subject BETA-APOLIGNANS en
dc.subject PHOTOCYCLIZATION en
dc.subject STEREOCHEMISTRY en
dc.subject 2,3-DIBENZYLIDENEBUTYROLACTONES
dc.subject PHOTOREACTIONS
dc.subject 2,3-dibenzylidenesuccinate
dc.title The complex photochemistry of 2,3-dibenzylidenesuccinates en
dc.type info:eu-repo/semantics/contributionToPeriodical
dc.type journal article en_US
dc.status Peer reviewed en
dc.identifier.doi http://dx.doi.org/10.1139/v04-143


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