Formation of phosphoranes from methyl maleanilates and related substrates with triphenylphosphine and their Wittig olefinations with aromatic aldehydes

  • V Balasubramaniyan
  • D B Tongare
  • S S Gosavi
  • S M Babar


An efficient method to obtain phospharanes from triphenylphosphine (TPP) and maleic anhydride (MA), dialkyl maleates, N-aryl maleimides and methyl N-aryl maleanilates is reported. These stabilised phosphoranes react with aromatic aldehydes to yieldE-olefins but fail to react with monoketones and 1,2-diketones. With the more reactive triketone, ninhydrin, the reaction is positive. The order of reactivity of these reagents in olefination appears to be imides=isomaleimides>maleanilates>dialkyl maleates>anhydrides.


Wittig reactions maleic acid derivatives stabilised phosphoranes 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Argade N P and Balasubramaniyan V 1988J. Prakt. Chem. 330 626CrossRefGoogle Scholar
  2. Armstrong A W, Coulton S and Ramage R 1976Tetrahedron Lett. 4311Google Scholar
  3. Awad W I, Kandile N G, Wassef W N and Mohamed M J 1989J. Prakt. Chem. 331 405CrossRefGoogle Scholar
  4. Barrett A G M, Broughton A, Atwood S and Gunatilaka A A L 1986J. Org. Chem. 51 494Google Scholar
  5. Bhatia V G 1984Preparation of anilic acid esters using novel sulphur and phosphorus reagents and a study of their reactions, Ph D thesis, University of PoonaGoogle Scholar
  6. Cooke M P and Manning P 1981Tetrahedron Lett. 22 381CrossRefGoogle Scholar
  7. Eyjolfsson R 1970Acta Chem. Scand. 24 3075CrossRefGoogle Scholar
  8. Gosney I and Rowley A G 1979 InOrganophosphorus reagents in organic synthesis (ed.) J I G Cadogan (London: Academic Press) chap. 2, pp. 27–28Google Scholar
  9. Hedaya E and Theodoropulos S 1968Tetrahedron 24 2241CrossRefGoogle Scholar
  10. Hoffmann H 1961Chem. Ber. 94 1331CrossRefGoogle Scholar
  11. McMurry J E and Donovan 1977Tetrahedron Lett. 2869Google Scholar
  12. Nair M D and Adams R 1961J. Am. Chem. Soc. 83 922CrossRefGoogle Scholar
  13. Osuch C, Franz J E and Zienty F B 1964J. Org. Chem. 29 3721CrossRefGoogle Scholar
  14. Patel M V, Balasubramaniyan P and Balasubramaniyan V 1979Indian J. Chem. B18 245Google Scholar
  15. Patil S V, Balasubramaniyan P and Balasubramaniyan V 1990Indian J. Chem. B29 124, 659Google Scholar
  16. Shaikh A S, Balasubramaniyan P and Balasubramaniyan V 1986Tetrahedron 42 2731CrossRefGoogle Scholar
  17. Tong H K and Isoe K S 1983J. Chem. Soc., Chem. Commun. 730Google Scholar
  18. Wani M J, Balasubramaniyan P and Balasubramaniyan V 1990Indian J. Chem. B29 1092Google Scholar
  19. Wani M J, Balasubramaniyan P and Balasubramaniyan V 1991Proc. Indian Acad. Sci. (Chem. Sci.) 103 621Google Scholar

Copyright information

© Indian Academy of Sciences 1993

Authors and Affiliations

  • V Balasubramaniyan
    • 1
  • D B Tongare
    • 1
  • S S Gosavi
    • 1
  • S M Babar
    • 1
  1. 1.Science Research Centre, Department of ChemistryHPT Arts and RYK Science CollegeNashikIndia

Personalised recommendations