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31.13.1.6 Method 6: Newman–Kwart Rearrangement of Phenols

DOI: 10.1055/sos-SD-031-00879

Rakitin, O. A.Science of Synthesis, (200731953.

An important synthetic approach to arenethiols is from the corresponding phenols. This reaction cannot be realized directly, but there are a number of multistep procedures. The most widely used of these methods is the NewmanKwart rearrangement, which consists of the successive preparation of the O-aryl thiocarbamate, the S-aryl thiocarbamate, and the arenethiol, as exemplified by the preparation of arenethiol 13 from phenol 10 via thiocarbamates 11 and 12 (Scheme 7).[‌35‌,‌36‌] Although this route appears lengthy, it seems to be reliable, and the yields are good in each step.

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