β-Sulphonylenamines. An X-ray and 1H nuclear magnetic resonance study of the stereochemistry of the isomeric β-chloromethylsulphonyl-β-methyl-α-morpholinostyrenes

Abstract

A study has been made, both in the solid state and in solution, of the stereochemistry of the components of the mixture of the isomeric β-chloromethylsulphonyl-β-methyl-α-morpholinostyrenes obtained among other products in the reaction between chloromethanesulphonyl chloride and (E)-β-methyl-α-morpholinostyrene in the presence of triethylamine. X-Ray analysis of two different kinds of manually separated crystals shows the presence of three conformational racemic rotamers of the same molecule with the E-configuration. Two of them coexist in the same crystal. The ¹H n.m.r. data give evidence for the presence in solution of an equilibrium mixture of the E-and Z-isomers. The position of equilibrium depends partially on the nature of the solvent.