SYNTHESIS AND CHARACTERIZATION OF S,S-, S,S,S-, AND THIOMORPHOLINYL-SUBSTITUTED NITRODIENE COMPOUNDS AND A STRUCTURAL STUDY

Abstract

S,S- and S,S,S-substituted nitrodienes 3a, 3b, and 4a were synthesized by reactions of 1,1,2,4,4-pentachloro-3-nitro-1,3-butadiene with some thiols 4-chlorobenzylmercaptan and 2-chlorobenzylmercaptan in ethanol in the presence of sodium hydroxide. Thiomorpholine ring substituted nitrodienes 6c and 6d and were obtained from the reactions of the mono(thio)substituted nitrodienes with thiomorpholine in dichloromethane. The single crystal X-ray structure of 4-(1-thiomorpholinyl)-4-(butylsulfanyl)-1,1,2-trichloro-3-nitro-1,3-butadiene (6c) is reported. In this present paper, the structures of new compounds were characterized by using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and Fourier transform infrared (FTIR) spectroscopy spectroscopic data.