Reactions of Methoxycarbonylcarbenes with 1,3-Disubstituted Propenes

摘要

The catalytic cyclopropanation of cis- and trans-1,3-dichlorpropenes with methyl diazoacetate in the presence of a copper catalyst was studied. The products composition and ratio were shown to depend on the spatial structure of 1,3-dichloropropene. The cis- and trans-1,3-dichloropropenes Ia and Ib are the major by-products in the allyl chloride production and have been described earlier. The individual isomers successfully are isolated in distillation process. The unsaturated compounds Ia and Ib are of interest as promising reagents for the fine organic synthesis. The reactions of allyl halides with alkyl diazoacetates in the presence of copper and rhodium catalysts were known to give both the C-X- and cyclopropanes adducts. In the present work the reaction of cis- and trans-1,3-dichloropropenes Ia and Ib with methyl diazoacetate in the presence of Cu(acac)_2 was examined.