Ring-closing metathesis in methanol and water

TA Kirkland, DM Lynn, RH Grubbs

Index: Kirkland, Thomas A.; Lynn, David M.; Grubbs, Robert H. Journal of Organic Chemistry, 1998 , vol. 63, # 26 p. 9904 - 9909

Full Text: HTML

Citation Number: 170

Abstract

The ring-closing metathesis (RCM) of acyclic dienes in both methanol and water has been achieved through the use of water-soluble ruthenium alkylidenes. These alkylidenes react readily with acyclic olefins in protic solvents, but they do not cyclize α, ω-dienes because of the instability of the resulting methylidene. Successful cyclization has been achieved through simple substrate modification incorporation of an olefin substituent allows ...