Synthesis and Crystal Structures of 4,4-Dichloro-2-nitro-1,1,3-tris(phenylsulfanyl)-buta-1,3-diene and 4,4-Dichloro-2-nitro-1,1-bis(phenylsulfanyl)-3-(phenylsulfinyl)-buta-1,3-diene

Abstract

Nitro-substituted polyhalogeno-1,3-butadienes possess valuable synthetic precursors for a variety of polyfunctionalized bioactive compounds 1 . According to a US patent, some thio-substituted dienes also exhibit high biological activity such as insecticide, herbicide and fungicide 2 .In recent years, certain mono-, di-, tris(thio) substituted compounds were obtained from the reactions of nitrodienes with thiols and dithiols [3][4][5][6][7][8][9] . There are some reports on the crystal structure of these compounds [10][11][12][13][14][15][16] . The oxidation reaction of organo sulphur compounds has been the focus of great interest recently in biochemistry and in industrial processes 17 . The reason for this is, partly due to the broad spectrum of biological properties of these compounds.Previous studies indicate that, sulfone and sulfoxide compounds are formed in the oxidation reaction of some thio ethers with diene groups [18][19][20][21] however this is the first study on crystal structure of sulfinyl-nitrobutadiene derivatives.Halogen derivatives of nitrobutadienes are suitable model objects for elucidating the features of nucleophilic vinylic substitution (SNVin) 22 . It is well known that in perhalo-2-nitrobuta-1,3-dienes, C-3 and especially C-1 position possesses profound electrophilic character because of the electron-withdrawing property of nitro group. This property allows regioselective substitution of one or two terminal vinylic chlorine substituents (C-1 position) in the nitro dichloro vinyl moiety of the dienes firstly. Third substitution of chlorine atom occurs at the C-3 position 16 .