[3+2]-Cycloaddition reactions of 2-phenyliodonio-1,3- dioxacyclohexanemethylide: Facile synthesis of fused dihydrofuran derivatives

Article abstract of DOI:10.1016/S0040-4039(98)01997-2

Iodonium ylide 2, derived from 1,3-cyclohexadione, undergoes thermal [3+2]-cycloaddition with acetonitrile, carbon disulfide and p, p'- dimethoxythiobenzophenone with Cu(acac)₂ catalysis to form the corresponding 5-membered heterocycles and alkene respectively. Photochemically 2 reacts with various alkenes and dienes to form dihydrofuran derivatives, key intermediates for paniculide A, B and pentalene synthesis.