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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

The 3-Methyl-1,3-butadienyl Phenyl Sulfoxide II. Utilization as a Michael Acceptor of Lithiated Protected Cyanohydrins. Syntheses of Tagetones and Ocimenones

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Pages 709-722 | Published online: 06 Dec 2006

References

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  • Goldmann , S. , Hoffmann , R. W. , Maak , N. and Geueke , K.-J. 1980 . Chem. Ber. , 113 : 831
  • Stork , G. and Maldonado , L. 1971 . J. Amer. Chem. Soc. , 93 : 5286 G. Stork, J.-C. Depezay and J. d'Angelo, Tetrahedron Letters, 389 (1975); A. Casares and L. A. Maldonado, Synth. Commun., 6, 11 (1976)
  • This was probably due to the fact that the silylated carbanion 4u is less stable than 2u;see S. Hünig and M. Oeller, Chem. Ber., 113, 3803 (1980)
  • Russell , G. A. and Becker , H.-D. 1963 . J. Amer. Chem. Soc. , 85 : 3406 B. G. James and G. Pattenden, J. C. S. Perkin I, 1195 (1974) and references cited therein; V. Ratoveloma-nana, C. Huynh and S. Julia, Compt. rend., 280 C, 1327 (1975); P. A. Bartlett, J. Amer. Chem. Soc., 98, 3305 (1976); H. J. Reich, J. J. Rusek and R. E. Olson, ibid., 101, 2225 (1979); L. V. Dunkerton and R. M. Ahmed, Tetrahedron Letters, 1803 (1980)
  • Hoffmann , R. W. 1979 . Angew. Chem. Int. Ed. Engl. , 18 : 563 see for examples of E/Z isomerization of the double bond of allylic sulfoxides
  • Chabardes , P. , Julia , M. and Menet , A. 1973 . Chem. Abstr. , 79 : 126671 For other Michael additions to dienylic sulfones see: 80, 26 750 (1974); J. J. Burger, T. B. R. A. Chen, E. R. de Waard and H. O. Huisman, Tetrahedron, 36, 1847 (1980)
  • Adams , D. R. , Bhatnagar , S. P. , Cookson , R. C. , Tuddenham , R. M. and Perkin , J. C. S. 1975 . 1741 (see also D. J. J. de Villiers, C. F. Garbers and R. N. Laurie, Phytochemistry, 10, 1359 (1971)
  • Crombie , L. , Kneen , G. , Pattenden , G. and Whybrow , D. 1980 . J. C. S. Perkin , For 13C-NMR investigation of terpenoid compounds see: I, 1711(B. M. Trost and T. R. Verhoeven, J. Amer. Chem. Soc., 102, 4730 (1980); R. E. K. Winter, F. Dorn and D. Arigoni, J. Org. Chem., 45, 4786 (1980); A. Okubo, H. Kawai, T. Matsunaga, T. Chuman, S. Yamazaki and S. Toda, Tetrahedron Letters, 4095 (1980)
  • Cazes , B. and Julia , S. 1977 . Synth. Commun. , 7 : 113
  • Malanco , F. L. and Maldonado , L. A. 1976 . ibid. , 6 : 515
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  • Guittet , E. and Julia , S. Synth. Commun. preceding communication
  • Menet , A. 1974 . Chem. Abstr. , 80 : 26 943
  • Uguen , D. , P. and Curie , M. 1977 . Paris VI(thèse de Doctorat d'Etat ès Sciences Physiques, Université
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  • Julia , M. and Badet , B. 1975 . Bull. Soc. Chim. France , : 1363 some [btilde]-phenylsulfonyl-ketones have been transformed into α, [btilde]-ethylenic ketones
  • Adams , D. R. For previous syntheses of tagetones and ocimenones, see et al.7 and references cited therein

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