Collect. Czech. Chem. Commun. 2002, 67, 1486-1492

Synthesis and Chemistry of Highly Fluorinated Oxepane-2,7-diols

Pamela J. Lombardi, Yonghong Gan and David M. Lemal*

Department of Chemistry, Dartmouth College, Hanover, NH 03755, U.S.A.


Reduction of dimethyl perfluoroadipate with Vitride yielded the title compounds, which were also prepared by dehydration of 1H,6H-perfluorohexane-1,1,6,6-tetrol. The configurations of the oxepanediols were assigned based on the crystal structure of the bis(tert-butyldiphenylsilyl) ether of the cis stereoisomer. Treatment with ethanolic HCl ring-opened the diols to 1H,6H-1,6-diethoxyperfluorohexane-1,6-diol, and dehydration with P4O10 gave perfluorohexanedial.

Keywords: Reductions; Cyclizations; Hemiacetals; Aldehydes; Oxepanes; Fluorinated compounds; X-Ray diffraction.

References: 13 live references.