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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 4
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Original Articles

A Useful Divinyl Ketone Equivalent

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Pages 211-218 | Received 12 Dec 1977, Published online: 06 Dec 2006

References

  • Danishefsky , S. and Migdalof , B. 1969 . J. Amer. Chem. Soc. , 91 : 2806
  • Danishefsky , S. , Crawley , L. S. , Solomon , D. M. and Heggs , P. 1971 . J. Amer. Chem. Soc. , 93 : 2356
  • Danishefsky , S. , Crawley , L. , Solomon , P. , Sax , M. , Abola , E. , Yoo , C. S. and Pletcher , J. M. 1972 . Tetrahedron Letters , : 961
  • The base induced (1 eq. of base) Michael addition of the first donor is shortly followed by dehydrohalogenation, thus exposing a new vinyl ketone (see ref. 1)
  • Danishefsky , S. , Yan , C. F. and McCurry , P. 1977 . J. Org. Chem. , 42 : 1819
  • Yates , P. and Eaton , P. 1960 . J. Amer. Chem. Soc. , 82 : 4436
  • Reich , H. J. , Renga , J. M. and Reich , I. L. 1975 . J. Amer. Chem. Soc. , 97 : 5434 H. L. Reich, I. L. Reich and J. M. Renga, ibid, 95, 5813(1973)
  • Sharpless , K. B. , Larier , R. F. and Teranishi , A. Y. 1973 . J. Amer. Chem. Soc. , 95 : 6137
  • Merrwein , H. and Schurman , W. 1913 . Ann. , 398 : 196
  • Melting points are uncorrected. Nmr spectra were measured on a Varian Associates T-60 Spectrometer. Chemical shifts are reported in parts per million (δ) relative to the internal standard, tetramethylsilane. Infrared spectra were recorded on a Perkin Elmer Infracord spectrophotometer. Low resolution mass spectra were obtained from an LKB-9000 spectrometer by direct insertion
  • House , H. O. , Czuba , L. J. , Gall , M. and Holmstead , H. D. 1969 . J. Org. Chem. , 34 : 2324
  • We see clear evidence for only one stereoisomer in the nmr spectrum of 6 though trace amounts of a second may be present. The stereochemistry is unassigned
  • Presumably, this substance is a mixture of diastereomers (differing in the relative configuration of the two asymmetric centers) which co-crystallize and do not differ in their spectral properties. We see no positive evidence for two diastereomers

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