COUPLING AND HYDROXYLATION OF LITHIUM AND GRIGNARD-REAGENTS BY OXAZIRIDINES

Oxaziridincs represent a unique class of three-member cdheterocyclic compounds which undergo novel thermal and photochemical transformations.1, 2 At present, the chemistry of these compounds is not well understood. Despite the fact that oxaziridines have been known for nearly 25 years,3 there appears to have been no study of the reactions of this class of compounds with organometallic reagents. By contrast, thereactions of oxiranes, aziridines, and thiiranes with these reagents have been extensively explored and constitute synthetically useful transformations. Oxiranes give ring-opened products resulting from attack of the lithium and Grignardreagent at the carbon atom adjacent to the oxygen.4 The situation for aziridines is somewhat more complicated, but similar ring-opened products have been described.5 Thiiranes, on theother hand, are attacked at sulfur by organolithium compoundsto afford the thiol and alkene stereospecifically.6, 7 Grignardreagents react with thiiranes in a manner similar to Grignard reagents with oxiranes and aziridines.8. © 1979, American Chemical Society. All rights reserved.