Alkynyliodonium salts in organic synthesis. Preparation of 2-substituted-3-p-toluenesulfonyldihydrofurans from 1-hydroxybut-3-ynyliodonium ethers via a formal Stevens shift of a carbon group.
[reaction: see text]p-Toluenesulfinate addition to 1-hydroxybut-3-ynyliodonium ethers triggers a sequence of reactions which ultimately delivers 2-substituted-3-p-toluenesulfonyldihydrofuran products along with 3-p-toluenesulfonyldihydrofuran as a major byproduct. A putative 1,2-alkyl shift within an unsaturated oxonium ylide (Stevens rearrangement) accounts for the oxygen-to-carbon transfer of the alkyl group.
Feldman
K S
KS
Department of Chemistry, The Pennsylvania State University, University Park 16802, USA.
Wrobleski
M L
ML
D002625:Chemistry, Organic; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009861:Onium Compounds / Q000737:chemistry*; D055601:Organic Chemistry Phenomena; D013450:Sulfones / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives / Q000737:chemistry*
D005663:Furans; D009861:Onium Compounds; D013450:Sulfones; D014050:Toluene