Journal of the American Chemical Society

An Attempted Fries Reaction with Thiolesters. The Formation of Trithioörthoesters1

DS Tarbell, AH Herz

文献索引：Tarbell; Herz Journal of the American Chemical Society, 1953 , vol. 75, p. 1668,1670

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被引用次数: 11

摘要

The Fries rearrangement of favorably substituted aryl thiolesters has not been realized, even in the presence of the strong Lewis acid, aluminum bromide. Instead, trithioorthoesters may be formed by partial cleavage of the thiolester, followed by the addition of the thiophenol to the ester carbonyl. Thus, phenyl thiolacetate upon treatment with boron fluoride or aluminum bromide yielded phenyl trithiolirthoacetate (I). Structure I had been previously assigned to ...