Journal
TETRAHEDRON
Volume 64, Issue 18, Pages 4108-4116Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.02.005
Keywords
photocycloaddition reactions; di-2-pyrones; diolefins; macrocyclic compounds
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Sensitized photocycloaddition reactions of 6,6'-dimethyl-4,4-[1,3-bis(methylenoxy)phenylene]-di-2-pyrone (1) with electron-poor alpha,omega-diolefins such as ethylene diacrylate (2a) and polyoxyethylene dimethacrylates (2b-d) afforded site- and stereoselective macrocyclic dioxatetralactones (3a-d) and (4b) having 18- to 25-membered rings across the C5-C6 and C5'-C6' double bonds, or C5-C6 and C3'-C4' double bonds in 1, respectively. Similar photoreactions of I with electron-rich alpha,omega-diolefins such as poly(ethylene glycol)divinyl ether (2e and 2f) afforded crown ether-type macrocyclic compounds (5e and 5f) having 18- and 21-membered rings across the C3-C4 and C3'-C4' double bonds in 1, respectively. The stereochemical features of 3b, 5e-xx, and 5e-nn were determined by the X-ray crystal analysis. The reaction mechanism was inferred by MO methods. (c) 2008 Elsevier Ltd. All rights reserved.
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