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

Waldemar Adam, Judit Halász, Zsigmond Jámbor, A. Lévai, Csaba Nemes, T. Patonay, Gábor Tóth

Research output: Contribution to journalArticle

16 Citations (Scopus)

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
Publication statusPublished - Feb 21 1996

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Tetralones
Stereochemistry
Epoxy Compounds
Isomers
Epoxidation
Silica Gel
Chromatography
Hydrogen Peroxide
Nuclear magnetic resonance spectroscopy
Oxidation
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and stereochemistry of the epoxides of 2-arylmethylidene-1-tetralones. / Adam, Waldemar; Halász, Judit; Jámbor, Zsigmond; Lévai, A.; Nemes, Csaba; Patonay, T.; Tóth, Gábor.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 4, 21.02.1996, p. 395-400.

Research output: Contribution to journalArticle

Adam, Waldemar ; Halász, Judit ; Jámbor, Zsigmond ; Lévai, A. ; Nemes, Csaba ; Patonay, T. ; Tóth, Gábor. / Synthesis and stereochemistry of the epoxides of 2-arylmethylidene-1-tetralones. In: Journal of the Chemical Society, Perkin Transactions 1. 1996 ; No. 4. pp. 395-400.
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