Regioselective amination of polyunsaturated ethers

Article abstract of DOI:10.1016/S0040-4020(01)88768-8

(Ethocycarbonyl)nitrene (NCO₂Et) adds selectively to methyl neryl ether, geranyl methyl ether, and allyl neryl ether. For all the substrates the main product (up to 50%) is the aziridine deriving from addition to the double bond remote from the oxygen atom. Competition experiments point to a different reactivity of the two kind of double bonds and these results are compared with those reported for similar substrates in other addition reactions.