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

A Asouti, LP Hadjiarapoglou

Index: Asouti, Amalia; Hadjiarapoglou, Lazaros P. Tetrahedron Letters, 1998 , vol. 39, # 49 p. 9073 - 9076

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Citation Number: 34

Abstract

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.