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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 7-8
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Original Articles

A Convenient Conversion of a 1,5-Diene to Tetrahydropyrans with Stereocontrol

Pages 1233-1237 | Published online: 24 Oct 2006

References

  • Present address: Fine Organics Ltd., Teesside Site, Seal Sands, Middlesbrough, Cleveland TS2 1UB, UK
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  • Paterson , I. , Boddy , I. and Mason , I. 1987 . Tetrahedron Lett. , 28 : 5205
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  • Amouroux , R. , Folefoc , G. , Chastrette , F. and Chastrette , M. 1981 . Tetrahedron. Lett. , 22 : 2259
  • Hoye , T. R. and Jenkins , S. A. 1987 . J. Amer. Chem. Soc. , 109 : 6196
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  • Russell , S. T. , Robinson , J. A. and Williams , D. J. 1987 . J. Chem. Soc., Chem. Commun. , : 351
  • Michael , J. P. , Ting , P. C. and Bartlett , P. A. 1985 . J. Org. Chem. , 50 : 2416
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  • Davis , F. A. and Chattopadhyay . 1986 . Tetrahedron Lett. , 27 : 5079
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  • Bartner , P. , Boxler , D. L. , Brambilla , R. , Mallams , A. K. , Morton , J. B. , Reichert , P. , Sancilio , F. D. , Surprenant , H. , Tomalesky , G. , Lukacs , G. , Olesker , A. , Thang , T. T. , Valente , L. and Omura , S. 1979 . J. Chem. Soc., Perkin Trans. 1 , : 1600 This compares with furnised natural rubber (13C nmr: 85.8, 83.9) and the model, 2-ethyl-5-(1-hydroxymethylethyl)-2-methyltetrahydrofuran (13C nmr: 85.9, 84.8, 83.3, 71.0, 70.7). Also, see data given in refs. 2(a) and 2(e). Ref. 5 gives data on 2-cyclohexyl-5-(1-hydroxymethylethyl)-tetrahydrofuran; Bartlett, P. A., Private Communication, gives 2-cyclohexyl-6,6-dimethyltetrahydropyran-5-ol (13C nmr: 74.7, 74.6, 73.7). Values for various tetrahydropyran-3-ols are given by

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