Generation, trapping and fate of alkylidenecarbene-iodonium ylides from the addition of NaN3 to alkynylphenyliodonium tosylates

Abstract Addition of NaN3 to RCC I + Ph· O − Ts results in novel alkylidenecarbene-iodonium ylides, 5, R(N 3 )CCIPh, that by either protonation, ylide transfer or insertion of the derived carbene R(N 3 )CC: give unique functionalized vinyl azides.