Abstract
3,5-Dialkyl-1,2,4-trithiolanes (I–IV) have been synthesized in reasonable yields by a new route ▪ involving chlorination of dialkyl disulfides to α-chloroalkyl sulfenyl chlorides, reaction with potassium iodide giving di-α-chloroalkyl disulfides and subsequent cyclization with sodium sulfide. All dialkyltrithiolanes synthesized exist in two isomeric configurations ( cis/trans), separable by preparative GLC or column chromatography over alumina. We were able to assign unequivocally the cis and trans configurations by use of the Nuclear Overhauser Effect. From the temperature dependence of the PMR spectra and from Aromatic Solvent Induced Shifts in the spectra it appeared that all dialkyltrithiolanes show pseudorotation: the relative abundance of each conformer is dependent on the bulk of the alkyl groups. The energy barrier for pseudorotation was estimated to be smaller than 6 kcal/mole.
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