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

✍ Scribed by Amalia Asouti; Lazaros P. Hadjiarapoglou

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 221 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01997-2

✦ Synopsis

lodonium yllde 2, derived from 1,3-cyclohexadlone, undergoes thermal [3+2]-cydoaddition with acetonitrile, carbon disulfide andp.

p'-dlmethoxythlobenzophenone with Cu(acac)2 catalysis to form the corresponding 5-membered heterocydes and alkene respectively. Photochemically 2 reacts with various alkenes and dieaes to form dihydrofuran derivatives, key intermediates for panicufide A, B and pentalene synthesis.