Abstract
[reaction: see text] The oxidation of 7,8-dithiabicyclo[4.2.1]nona-2,4-diene 7-exo-oxide with dimethyldioxirane (DMD) provided the 7-exo-8-exo-dioxide, the structure of which was determined by X-ray crystallography [S-S 2.341(2) A and 90 degree angle O-S-S-O 4.1(3) degrees ]. The exo attack of DMD to give the exo,exo-dioxide was kinetically more favorable than the endo attack to give the endo,exo-dioxide. DFT calculations showed that the exo,exo-dioxide is thermodynamically more stable than the other stereoisomers.
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