V. Piccialli, M. Graziano
2001
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The reaction of the 3-alkyl-substituted and 3,3-dialkyl-substituted ethyl 2,2-dimethoxycyclopropanecarboxylates 1 – 3 with m -CPBA in CH 2 Cl 2 leads to the formation of the β-hydroxyacid derivatives 4 – 6 via two related processes involving the scission of both the C 1 C 2 and C 2 C 3 bonds and consequently to the degradation of the original cyclopropane carbon skeleton (extrusion of the C-2 carbon). Cis - and trans -2-ethoxycyclopropanecarboxylic acid ethyl esters 9 and 10 , respectively, structurally related to 1 – 3 , are unreactive under the same conditions. A hypothesis explaining the observed reactivity is formulated.