Trans Dialkoxylation of Cyclic Alkenes: A Prévost-Type Reaction

Abstract

Reaction of anhydrous silver perchlorate, sym-collidine, and iodine (2:1:1 molar ratio) with cyclic alkenes and an excess of an alcohol in CH₂Cl₂ affords trans-1,2-dialkoxycycloalkanes in high yields and purity. The reaction occurs via initial formation of the trans-iodoethers, which undergo Ag-assisted iodide abstraction to give the trans-diethers.

Keywords

alkenes - iodoalkoxylation - dialkoxylation - silver perchlorate - collidine

References

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1

Professor Emeritus, Villanova University, Villanova, PA 19085, USA.

2

Ph.D., Villanova University, 1992. Current address: Quaker Chemical Corp., Conshohocken, PA 19428, USA.

3

M.S., Villanova University, 1987. Current address: Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, NJ 08540, USA.

4

M.S., Ph.D., Villanova University, 1983, 1986. Current address: Quaker Chemical Corp., Conshohocken, PA 19428, USA.