Stereoselective epoxidation of 2-arylidene-1-indanones and 2-arylidene-1-benzosuberones |
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| Authors: | W. Adam J. Halász Z. Jámbor A. Lévai C. Nemes T. Patonay G. Tóth |
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| Affiliation: | (1) Institute of Organic Chemistry, University of Würzburg, D-97094 Würzburg, Germany;(2) Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry, Technical University, H-1111 Budapest, Hungary;(3) Department of Organic Chemistry, Lajos Kossuth University, H-4010 Debrecen, Hungary |
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| Abstract: | Summary Oxidation of the (E) and (Z) isomers of 2-arylidene-1-indanones (1) and 2-arylidene-1-benzosuberones (4) by alkaline hydrogen peroxide (methodi) afforded the spiroepoxidestrans-2a–g andtrans-5a–g from both isomers as sole products in high yields. On the other hand, dimethyldioxirane epoxidation(methodii) of the (E) isomers1a–g and4a–g gave the correspondingtrans spiroepoxides in good yields, whereas the (Z) isomers1a,c,e and4a,c,e led to thecis spiroepoxides in moderate yields. Dimethyldioxirane oxidation (methodii) of (Z)-1c and (Z)-4c,e gave diones3c and6c,e as by-products as well. Epoxidation of (Z)-1a,c,e and (Z)-4a,c,e bym-chloroperoxybenzoic acid (methodiii) resulted inca. 6:1 mixtures ofcis-2a,c,e andtrans-2a,c,e orcis-5a,c,e andtrans-5a,c,e spiroepoxides.Dedicated to Prof.W. Fleischhacker on the occasion of his 65th birthday |
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| Keywords: | 2-Arylidene-1-indanones 2-Arylidene-1-benzosuberones Dimethyldioxirane Stereoselective epoxidations Epoxides |
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