H-1 and C-13 NMR Study Of some polychlorobuta-1,3-diene derivatives

Because of the upsurge of interest in polychlorobuta-1,3-diene derivatives as uncommon contaminants in underground water, seven congeners, the three p entachloro- and four tetrachloro- [(Z)- and (E)-1,1,3,4-tetrachloro-, 1,1,4 ,4-tetrachloro and (Z,Z)-1,2,3,4-tetrachloro]buta-1,3-dienes, were synthesi zed and their H-1 and C-13 NMR chemical shifts, (n)J(H-1,H-1) and (n)J(C-13 ,H-1) coupling constants were measured. The C-13 NMR spectra were recorded in perdeuteroacetone with and without proton decoupling. In addition, to as sign the C-13 NMR spectrum of 1,1,2,4,4-pentachlorobuta-1,3-diene, a 2D-INA DEQUATE C-13 experiment was performed. The present results were compared wi th literature data on organochlorine compounds and possible conformations a re discussed. (C) 1998 John Whey & Sons, Ltd.