Tetrahedron Letters

A new synthetic route to aryl hydroxysulfonamides via a novel Fries-type rearrangement of aryl N, N-dialkylsulfamates

GA Benson, PJ Maughan, DP Shelly, WJ Spillane

文献索引：Benson; Maughan, Patrick J; Shelly, Declan P; Spillane, William J Tetrahedron Letters, 2001 , vol. 42, # 49 p. 8729 - 8731

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被引用次数: 11

摘要

In this communication, we report a novel thia-Fries rearrangement (Scheme 1) in which a series of ten aryl N,N-dialkylsulfamates 1 have been isomerised to para-2 and/or ortho-3-hydroxysulfonamides in good yields (Table 1). This is a new and efficient method for synthesising sulfonamides bearing an -OH functionality. ... Since the original report of Rittler 1 of the Fries rearrangement giving hydroxydiarylsulfones, there have been numerous literature references to this ...