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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 9
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Original Articles

Reactions of 1,2-Epoxy-2-Methyl-3-butene with Lithio Derivatives of Allylic Sulfoxides. Syntheses of 2,6-Dimethylocta-3,7-dien-2,6-diol and of 5,8-Dehydro-4-0xo-nerolidol

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Pages 723-732 | Published online: 06 Dec 2006

References

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  • Hainaut , D. , Toromanoff , E. and Demoute , J.-P. 1973 . Chem. Abstr. , 78 : 147 To our knowledge, there is only one example: 378(.For a review of allylic sulfoxides as useful intermediates in organic synthesis, see D. A. Evans and G. C. Andrews, Accounts Chem. Research, 7, 147 (1974)
  • Clinet , J.-C. and Julia , S. 1978 . J. Chem. Research , (S) 125, (M) 1714
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  • Okamura , H. , Mitsuhira , Y. , Miura , M. and Takei , H. 1978 . Chem. Letters , : 517 The reaction of epoxides: with 1-arylsulfinyl-1-alken-1-yl lithium derivatives afforded small yields of addition compounds, and is sluggish with α-lithium derivatives of allenyl phenyl sulfoxides, R. C. Cookson and Ph. J. Parsons, J. C. S. Chem. Comm., 822 (1978)
  • Takaoka , D. and Hiroi , M. 1976 . Phytochemistry , 15 : 330 (for a partial synthesis of this diol from the photo-hydroperoxide of linalol, see T. Matsuura and Y. Butsu-gan, Chem. Abstr., 69, 87 201 (1968)
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  • Kuliev , A. M. , Dzhafarov , A. A. and Mamedov , F. N. 1968 . Chem. Abstr. , 68 : 29 An authentic sample of compound 8 has been prepared following a described procedure: 373(I. N. Azerbaev, L. A. Tsoi, A. B. Asmanova and V. S. Bazalitskaya, Chem. Abstr., 86, 189 368 (1977)

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