Phenyliodonium 1,4-dipoles

Photochemical reactions of 1,4-phenyliodonium dipoles leading to the formation of cyclic compounds... 

Iododiaryl ethers from 1,4-phenyliodonium dipoles Dipole Product Yield (%) Ref. 

Phenyliodonium sulfate 289, which is obtained from the reaction of iodo-sobenzene and sulfur trioxide at -50°C, behaves as a 1,4-dipole in the reactions with several alkenes (86ZOR450) to give intermediate [4 + 2] cycloadduct 290. Decomposition of this unstable adduct affords cyclic sulfates 291 (Scheme 73). Likewise, another 1,4-dipole 292 undergoes cycloaddition reaction to give cyclic sulfone 293 (88ZOR888). The 1,4-dipole 292 thermally decomposes to give 294 (86DOK1374) (Scheme 74). 

Phenyliodonium Zwitterions Preparation. Reactivity of Iodine-Carbon Ylides. Reactivity of Iodine-Nitrogen Ylides. Reactivity of 1,4-dipoles. 

---