Indole-containing 2-Nitroethenylphosphonates: Synthesis and Structure

Abstract

A method was developed for preparing first representatives of phosphorylated nitrovinylindoles, bis(2-chloroethyl) 1-(indol-3-yl)- and bis(2-chloroethyl) 1-(1-alkylindol-3-yl)-2-nitroethenylphosphonates, and the structures of these compounds were studied. The spectroscopic data and results of dipole moment measurements show that the molecules have E configuration with s-cis arrangement of the multiple bond and phosphoryl group. X-ray studies have shown that the molecules of the first compound, having the E-s-cis form in the solid phase also, exist in the crystal in the form of enantiomeric pairs. They are involved in inter- molecular hydrogen bonds to form infinite chains.