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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 12
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Original Articles

The Preparation of 4,5-Dihydro-5-Phenyl-5-(2-Phenylethenyl)Isoxazoles, 4,5-Dihydro-5-Methyl-5-(2-Phenylethenyl)Isoxazoles, or 4,5-Dihydro-5,5-DI-(2-Phenylethenyl)Isoxazoles from Dilithiated C(α),O-Oximes and Select α,β–-Unsaturated Ketones

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Pages 2175-2189 | Received 10 Jun 1999, Published online: 04 Dec 2007

REFERENCES AND NOTES

  • Since several names have been used for each of these compounds, the following abbreviated names are used: a. 4,5-dihydroisoxazole: isoxazoline or 2-isoxazoline; b. (2E)-1,3-diphenyl-2-propen-1-one: trans-chalcone [e.g., the name used by Aldrich Chemical Co]; c. (1E, 4E)-1,5-diphenyl-1,4-pentadien-3-one: dibenzalacetone [another name also used, trans, trans-dibenzilidene-acetone]; d. (3E)-4-phenyl-3-buten-2-one: benzalacetone [name also used, trans-4-phenyl-3-buten-2-one]. e. 2-phenylethenyl: styryl
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  • Each of the apparent quartets has J/δν < 8, and the chemical shifts are recorded as doublets
  • Silverstein , R. M. , Bassler , G. C. and Morrill , T. C. 1991 . “Spectrometric Identification of Organic Compounds,” , fifth edition , 24 New York, New York : John Wiley and Sons, Inc. . a. Fourier Transform infrared spectra (paraffin oil mulls) were obtained with a Nicolet Impact 410 FT-IR. b. 1H NMR and 13C NMR spectra were obtained with a Varian Associates Mercury Oxford 300 MHz nuclear magnetic resonance spectrometer, and chemical shifts are recorded in δ ppm downfield from an internal tetramethylsilane (TMS) standard. c. A DEPT spectrum was taken on several representative samples to determine the chemical shift of the methylene carbon (C-4) of the isoxazoline ring. d. The assignment is consistent with the chemical shifts noted for oximes, δ 158.–159.2 ppm. See also
  • Shriner , R. L. , Hermann , C. K. F. , Morrill , T. C. , Curtin , D. Y. and Fuson , R. C. 1997 . “The Systematic Identification of Organic Compounds,” , seventh edition , 323 New York, New York : John Wiley and Sons, Inc. .
  • a. Melting points were obtained with a Mel-Temp II melting point apparatus in open capillary tubes and are uncorrected. b. Combustion analyses for C, H and N were performed by Quantitative Technologies, Inc., P.O. Box 470, Salem Industrial Park, Bldg., 5, Whitehouse, NJ 08888.
  • Isochronous: two absorptions.

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