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13.30.4.3.3 Method 3: Smiles Rearrangement

DOI: 10.1055/sos-SD-013-01452

Brigas, A. F.Science of Synthesis, (200413906.

The Smiles rearrangement is an intramolecular nucleophilic displacement reaction under basic or acidic conditions, involving the replacement of a diarylsulfanyl function with an oxygen or nitrogen function present in one of the aryl groups to give a diaryl ether or diaryl amine, respectively. In the case of 1-substituted 5-sulfanyl-1H-tetrazoles, an amine or hydroxy group also present in the 5-position substituent displaces the sulfanyl group at C5 to give a 1-substituted 1H-tetrazol-5-amine or 1-substituted 1H-tetrazolyl ether;[‌248‌,‌249‌] the latter are useful in the synthesis of vinylsilanes.[‌247‌]

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References


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