Tetrahedron letters

Ring cleavage of THP and THF ethers using dimethylboron bromide

Y Guindon, MA Bernstein, PC Anderson

Index: Guindon, Yvan; Bernstein, Michael A.; Anderson, Paul C. Tetrahedron Letters, 1987 , vol. 28, # 20 p. 2225 - 2228

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Citation Number: 33

Abstract

Abstract The reaction of dimethylboron bromide with THP and THF ethers was studied. Under conditions of kinetic control, these reactions proceed by selective cleavage of the ring carbon—oxygen bond to give acyclic α-bromo ethers. Treatment of these intermediates with a variety of nucleophiles gives ring-opened products.