Tetrahedron Letters p. 8469 - 8470 (1999)
Update date:2022-08-12
Topics:
Graziano, M. Liliana
Piccialli, Vincenzo
The reaction of ethyl 2,2-dimethoxycyclopropanecarboxylates 1-3 with lead tetraacetate (Pb(OAc)4, LTA) in benzene leads to the oxidative scission of the C1-C2 bond. Monoalkylated fumaric acid diesters 4 and 5 are obtained from 3-alkylcyclopropanes 1 and 2, respectively, along with dimeric species for which we propose the unusual anhydride bis-acetal structure 6 or 7, respectively. Reaction of 3,3-dimethylcyclopropane 3 with LTA produces the 3-acetylsuccinate derivative 8 as the sole reaction product.
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