Thioether epoxides

Oxygen and sulfur as nucleophiles ethers, esters, thioethers, epoxides... 

Sulfonyloxaziridines were recently proposed as O-transferring reagents. Oxaziridine (89) converted thioethers to sulfoxides (90) and diaryl disulfides into their 5-oxides (91) (78TL5171). Epoxidations are also possible (81TL917). 

The reactivity of epoxides can be modified by various proximal functionality. For example, 2,3-epoxy sulfides 118 are converted to the corresponding TMS-thiiranium species 119 upon treatment with TMS triflate. This intermediate reacts with O-silyl amides regiospecifically to form l-substituted-3-hydroxy-2-thioethers (e.g., 120). Simple primary amines undergo polyalkylation, but imines can be used as an indirect amine equivalent <96TET3609>. 

The preparation of novel triazole-containing 20-22 membered macrocyclic azacrown ether-thioethers was reported <96JCR(S)182> and the first selective synthetic method fra the synthesis of dicyanotriazolehemiporhyrazines was published <96JOC6446>. 1,2,4-Triazole-containing polyimide beads were prepared and employed as Mo(VI) epoxidation catalyst supports, liie 1,2,4-nitronyl nitroxide 29 was also synthesized and found to have remarkable magnetic properties <96AM60>. 

ALCOHOLS AND THIOLS FROM ETHERS, EPOXIDES AND THIOETHERS... 

ETHER, EPOXIDE, THIOETHER - ETHER, EPOXIDE, THIOETHER... 

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