Journal
TETRAHEDRON
Volume 57, Issue 52, Pages 10319-10328Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)01058-4
Keywords
alkylation; radicals and radical reactions; 1,4-diketones; photochemistry; prostanoids
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Photosensitized hydrogen abstraction from 2-alkyl-1,3-dioxolanes by triplet benzophenone gives the corresponding 1,3-dioxolan-2-yl radicals and these are trapped by alpha,beta -unsatured ketones yielding monoprotected 1,4-diketones. With open chain ketones (3-buten-2-one and 4-penten-3-one) the yields are low and competitive pathways in part consume the radicals. With cyclic enones however, yields are good as tested with cyclopentenone, cyclohexenone and 4-hydroxy-cyclopentenone. More generally, this is a viable alternative for the synthesis of 1,4-diketones via radicals while the thermal initiation gives only low yield. The reaction cannot be extended to strongly stabilized radicals, such as the 2-phenyl-1,3-dioxolanyl radical. (C) 2001 Elsevier Science Ltd. All rights reserved.
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