Ring Expansions of 2-Haloethynyl-2-norbornanols

✍ Scribed by Elsa Djuardi; Pakorn Bovonsombat; Edward Mc Nelis

• Book ID: 104204706
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 785 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89294-2

✦ Synopsis

Z-Haloethvnvl-2-norbomanols react with iodine and Kosefs reagent in acetonitrile to afford two ring-expanded products, 2-[(Z)-haloiodomethylidene]bicyclo[3.2.&ctan-3-one and 3-[(Z)haloiodomethylidene]bicyclo[3.2.l]octan-Zone. These results contrast with the 2-haloethynyl-2bomanols whiih lead to the corresponding 3-octanones.

We have been examining the reactions of a-alkynols with iodonium-producing reagents because they represent methods of forming a-iodoenones. @-iodoenones and mixed P$-bromoiodoenones.14