Tetrahedron letters

Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents

PR Blakemore, MS Burge, MA Sephton

Index: Blakemore, Paul R.; Burge, Matthew S.; Sephton, Mark A. Tetrahedron Letters, 2007 , vol. 48, # 23 p. 3999 - 4002

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Citation Number: 11

Abstract

The reactions of syn-1-haloethyl p-chlorophenyl sulfoxides (halogen= Cl, Br) with main- group organometallic reagents (n-BuMgCl, MeLi, n-BuLi, s-BuLi, and t-BuLi) in THF and PhMe solvents were examined. Product distributions were analyzed to determine the extent of competing sulfoxide ligand exchange, halogen–metal exchange, and deprotonation reaction pathways. A combination of t-BuLi in PhMe was optimal for initiation of sulfoxide ...