Formation of phosphoranes from methyl maleanilates and related substrates with triphenylphosphine and their Wittig olefinations with aromatic aldehydes
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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.
KeywordsWittig reactions maleic acid derivatives stabilised phosphoranes
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- Armstrong A W, Coulton S and Ramage R 1976Tetrahedron Lett. 4311Google Scholar
- Barrett A G M, Broughton A, Atwood S and Gunatilaka A A L 1986J. Org. Chem. 51 494Google Scholar
- 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
- 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
- McMurry J E and Donovan 1977Tetrahedron Lett. 2869Google Scholar
- Patel M V, Balasubramaniyan P and Balasubramaniyan V 1979Indian J. Chem. B18 245Google Scholar
- Patil S V, Balasubramaniyan P and Balasubramaniyan V 1990Indian J. Chem. B29 124, 659Google Scholar
- Tong H K and Isoe K S 1983J. Chem. Soc., Chem. Commun. 730Google Scholar
- Wani M J, Balasubramaniyan P and Balasubramaniyan V 1990Indian J. Chem. B29 1092Google Scholar
- Wani M J, Balasubramaniyan P and Balasubramaniyan V 1991Proc. Indian Acad. Sci. (Chem. Sci.) 103 621Google Scholar