33468-98-3Relevant academic research and scientific papers
Interaction of (α-Haloalkyl)thiiranes with Nucleophilic Reagents. II. Reaction of (α-Chloroalkyl)thiiranes and Epihalohydrins with N,N′-Dimethylethylenediamine
Tomashevskii,Sokolov,Potekhin
, p. 583 - 588 (2007/10/03)
The (chloromethyl)thiirane reacts with N,N′-dimethylethylenediamine at heating in toluene to yield a mixture of 1,4-dimethylpiperazine-2-methanethiol and hexahydro-1,4-dimethyl-1,4-diazepine-6-thiol in 2: 1 ratio. The 2-methyl-2-(chloromethyl)thiirane under similar condition forms only the respective diazepine homolog in a low yield, while the diastereomers eritro- and threo-(1-chloroethyl)thiirans react stereospecifically to afford the corresponding eritro- and threo-α,1,4-trimethylpiperazine-2-methanethiols, and 2,2-dimethyl-3-(chloromethyl)thiirane does not react at all. The behavior of epihalohydrins in reaction with the N,N′-dimethylethylenediamine is similar to that of their thioanalogs. The specific features of these reactions are discussed from the viewpoint of the known competition between the intramolecular cyclization and nucleophilic opening of the cycle in unsymmetrically substituted thiiranes (oxiranes).
