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Synlett 1997; 1997(1): 126-128
DOI: 10.1055/s-1997-707
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Condensations of Crotonate Arsonium Ylide with Conjugated Carbonyl Compounds

Cornelis M. Moorhoff*
  • *Department of Chemistry, University of Tasmania, GPO Box 252C, Hobart, Tasmania, Australia 7001
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Publication Date:
22 March 2004 (online)

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Condensations of methyl 4-(triphenylarsoranylidene)-2-butenoate 1a and conjugated carbonyl compounds give 1,3-cyclohexadiene-1-carboxylates and/or acyclic trienes in superior yields compared to the condensations with the phosphonium analogue 1b. However, the reaction of 1a and ethyl 2-cyano-5-methyl-2,4-hexadienoate 7 gave a mixture of two diastereomeric trans-bisvinylcyclopropanecarboxylates 9.

methyl 4-(triphenylarsoranylidene)2-butenoate - Michael-Wittig - 1,3-cyclohexadienecarboxylates - cyclopropanation - trans-bisvinylcyclopropanecarboxylates

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