M. Graziano, M. Lasalvia, V. Piccialli
Jan 22, 1996
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The reaction of ethyl 2,2-dimethoxycyclopropane-1-carboxylates 1a-d and methyl 2,2,6,6-tetramethoxybicyclo[2.2.0]hexane-1-carboxylates 5a and 5b with RuO 4 in CCl 4 at room temperature leads in both cases to the oxidative ring opening by regioselective scission of the electron-rich C1C2 bond for 1a-d , and both C1C2 and C1C6 bonds for 5a and 5b . Methyl ethyl oxobutanedioates 2a-d were obtained in the first case while the 3-substituted ethyl methyl 2-oxopentanedioates 6a and 6b in the second one. In the same reaction conditions, cyclopropanes substituted with electron withdrawing groups, namely cyclopropyl methyl ketone ( 3a ) and cyclopropane-1,1-dicarboxylic acid ( 3b ) are unreactive; methyl 2,2-dimethoxycyclobutane-1-carboxylate 4 is unreactive as well.