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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 14
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Original Articles

Unexpected Solvent Effect of HMPA. Directed Selectivity of a Semistabilized Arsonium Ylide towards Carbonyl Compounds: The Case of Cinnamyl Triphenylarsonate

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Pages 1193-1196 | Published online: 05 Dec 2006

References

  • Yaozeng , Huang and Yanchang , Shen . 1982 . Adv. Organometal. Chem. Edited by: Stone , F. G. A. and West , J. R. Vol. 20 , 115 New-York : Academic Press . a)in, Eds
  • Trippett , S. and Walker , M. A. 1971 . J. Chem. Soc. C , : 114
  • Gosney , I. , Lillie , I. J. and Lloyd , D. 1977 . Angew. Chem. Int. Ed. Engl. , 16 : 487
  • Tewari , R. S. and Chaturvedi , S. C. 1977 . Tetrahedron Letters , : 3843 In this paper the authors reported that both solvent and base could have a determinent effect on the reaction course
  • In the solvent system used, ylides less stabilised than 1 lead preferentially to epoxydes, while the more stabilised one to double bounds
  • Bergelson , L. D. and Shemyakin , M. M. 1963 . Tetrahedron , 19 : 149 In this paper a similar effect was postulated to explain the steric course of a Wittig reaction in the presence of Lewis bases
  • Still , W. C. and Novack , V. J. 1981 . J. Am. Chem. Soc. , 103 : 1283
  • La Rochelle , R. N. , Trost , B. M. and Krepski , L. 1971 . J. Org. Chem. , 36 : 1126
  • Beny , J. P. , Pommelet , J. C. and Chuche , J. 1981 . Bull. Soc. Chim. France , : 369
  • All the compounds was identified by NMR, IR, combustion analysis and the yields based on the carbonyl compound

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