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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 2
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Original Articles

α-and γ-Substitution Reactions of Cyclic γ-Acetoxy-α,β-Unsaturated Esters with a Novel Reagent BuCu-AlCl3

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Pages 119-125 | Received 22 Aug 1979, Published online: 05 Dec 2006

References

  • Petersen , J. M. 1958 . Acta Chem. Scand. , 12 : 2007 2046 For reactions of acyclic enoate esters; G. H. Posner:“Organic Reactions”, Vol. 19, p. 25 (1972) and the references cited therein. J. Klein and S. Zitrin: J. Org. Chem., 36, 666 (1970). H. O. House: Acc. Chem. Res., 9, 59 (1976)
  • Yamamoto , Y. and Maruyama , K. 1978 . J. Amer. Chem. Soc. , 100 : 3240 For report on the reaction of enoate esters and enoic acids with a new reagent RCu.BF3, see
  • Posner , G. H. 1975 . Organic Reactions , Vol. 22 : 286 For reactions of allylic acetates; R. J. Anderson, C. A. Henrick, and J. B. Siddall: J. Amer. Chem. Soc., 92, 735 (1970). P. Rona, L. Tökes, J. Tremble, and P. Crabbé: J. Chem. Soc. Chem. Commun., 43 (1969). R. J. Anderson, C. A. Henrick, J. B. Siddall, and R. Zurflüh: J. Amer. Chem. Soc., 94, 5379 (1972). H. L. Goering and V. D. Singleton, Jr.: J. Amer. Chem. Soc., 98, 7854 (1976)
  • Kreft , A. 1977 . Tetrahedron Letters , : 1035 For reaction of allylic mesitates
  • Tanigawa , Y. , Kanamura , H. , Sonoda , A. and Murahashi , S.-I . 1977 . J. Amer. Chem. Soc. , 99 : 2361 For α- and γ-substitutions of the hydroxyl group of allylic alcohols; Y. Tanigawa, H. Ohta, A. Sonoda, and S.-I. Murahashi: J. Amer. Chem. Soc., 100, 4610 (1978)
  • Maruyama , K. and Yamamoto , Y. 1977 . J. Amer. Chem. Soc. , 99 : 8068 For substitution reaction of allylic halides with RCu.BF3
  • Descoins , C. , Henrick , C. A. and Siddall , J. B. 1972 . Tetrahedron Letters , : 3777 Reaction of an acyclic γ-acetoxy-α,β-unsaturated derivative with lithium dioctylcuprate has been reported, however, the structures of the products were not clarified
  • Felkin , H. and Swierczewski , G. 1975 . Tetrahedron , 31 : 2735 For hydrogenolysis with or without allylic rearrangement of allylic acetates with “Reducing Grignard Reagents”; and the references cited therein. See also A. Claesson and C. Sahlberg: Tetrahedron Letters, 5049 (1978)

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