Oxaziridine reactions with thiocyanates

Experiments with cyclic thioethers (80JCS(P1)1693), thiourea, thiocyanate and ethyl xan-thate always led to destruction of oxaziridines (73AJC2159). Products of complicated consecutive reactions could be isolated but only with some difficulty, e.g. (92) from a reaction with carbon disulfide (74JOC957), and (93), obtained by trapping with butadiene a product of a reaction between an oxaziridine and a thiirane (80JOC1691). 

Intermediates in Reactions.— Attempts to prepare thiaziridines or selenaziridines by treatment of oxaziridines (133) with thiourea, potassium thiocyanate, potassium ethylxanthate, potassium selenoxanthate, and triphenylphosphine sulphide gave imines (135) instead, although... 

The treatment of simple and fused oxaziridines with sulfur-containing nucleophiles such as thiourea, potassium thiocyanate, potassium ethyl-xanthate, potassium selenocyanate, and triphenyl-phosphine sulfide resulted in the formation of the related imines, most probably—in analogy to the results of the treatment of oxiranes with the same reagents—via the corresponding thiaziridine intermediate. The proposed reaction mechanism is given in Scheme 8 <73AJC2159>. 

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See also in sourсe #XX -- [ ]

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