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Oxidation of di-1-adamantyltetrathiolane with dimethyldioxirane (DMD) in dichloromethane and acetone gave di-1-adamantyldithiirane 1-oxide. Similarly, reaction of 1-adamantyl-t-butyltetrathiolane with DMD gave (1RS,3SR)- and (1RS,3RS)-1-adamantyl-t-butyldithiirane 1-oxides. In the reactions, intermediary formation of tetrathiolane 1-oxides was suggested by low-temperature 13 C NMR.
The reaction of 5,6-dithiabicyclo[2.1.1]hexane derivatives with OXONE in a two-phase mixture of dichloromethane and water gave the corresponding dithiirane derivatives which were stable in solution. The formation of the dithiiranes were proved by UV-Vis spectra and chemical transformations. The reaction of 7,8-dithiabicyclo[4.1.1]octane derivatives with OXONE gave the corresponding cis-dithiirane...
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