The Formation of 7-Oxabicyclo[4.2.0]octanes and 6-Oxabicyclo[3.2.1]octanes via Cationic Iodocyclization

Abstract

Several 2-cyclohexenemethanol derivatives were subjected to cationic iodocyclization. Two product types were formed: the fused 7-oxabicyclo[4.2.0]octane, and the bridged 6-oxabicyclo[3.2.1]octane. The degree of substitution in the alkenol determined the ratio of the products, with aromatic substituents leading to the formation of the fused system as the major product.

Keywords:

• Oxabicyclooctane
• Etherification
• Oxetane

Acknowledgments

This work was supported by the Department of Chemistry at California State University, Chico. Summer support was provided by the CSU Chico Research Foundation Summer Scholars Program. The departmental Varian Mercury VX300 NMR spectrometer was obtained through an NSF-CCLI grant by Prof. David B. Ball. Thanks also go to Will Chrisman at the University of California, Santa Barbara, for 2D NMR of compounds 10f and 11f.