Synthesis and stereochemistry of the epoxides of 2-arylmethylidene-1-tetralones

Waldemar Adam, Judit Halász, Zsigmond Jámbor, Albert Lévai, Csaba Nemes, Tamás Patonay, Gábor Tóth

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Abstract

Oxidation of both the E and Z isomers of the 2-arylmethylidene-1-tetralones 1 by alkaline hydrogen peroxide afforded the spiroepoxides trans-2a-g as sole products in high yields. In contrast, the dimethyldioxirane epoxidation of the E isomers 1a-g gave the corresponding trans spiroepoxides in good yields, while the Z isomers 1a,c,e yielded the respective cis spiroepoxides in moderate yields. Epoxidation of (Z)-1a,c,e by m-chloroperoxybenzoic acid yielded ca. 6:1 mixtures of cis-2a,c,e and trans-2a,c,e spiroepoxides. Separation of the isomeric epoxides was achieved by silica gel chromatography and their structures, relative configurations and stereochemistry were elucidated by NMR spectroscopy.

Original languageEnglish
Pages (from-to)395-400
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number4
DOIs
Publication statusPublished - Feb 21 1996

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ASJC Scopus subject areas

  • Chemistry(all)

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