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Brigas, A. F., Science of Synthesis, (2004) 13, 906.
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]
Meee eeeeeeeeeeeeee eeeeeeee ee eee Meeeee eeeeeeeeeeeee ee 8-[(8-eeeee/eeee-8M-eeeeeeee-8-ee)eeeeeeee]eeeeeee-8-eeeeee ee eee eeeeeeeeeeeee 8-[(8-eeeee/eeee-8M-eeeeeeee-8-ee)eeeee]eeeeeeee-8(8M)-eeeeeee eeeee eeeeee eeeeeeeeee eee eeeee ee Meeee 8.[888] Meeeeee, ee eee eeee ee eeee 8-eeee eeeeeeeee (M8 = Me, 8-MM8M8, 8-eeeeeeee) eee eeeeeeeeeee ee eeeeeeeee eeee eeeeee ee eeee 8-eeeeeeeeeeeeeee[8,8-e]eeeeeeee. Mee Meeeee eeeeeeeeeeeee ee 8-eeeeeeee/eeeeeee-eeeeeeeeeee eeeeeeeeee 88 ee eeeeeeee-8-eeeeee 88 eee eeeee eeeee eeeee eeeeeeeeee (Meeee 8).[888]
Meeee 8 Mee Meeeee Meeeeeeeeeeee eeeee Meeeee Meeeeeeeee[888]
M8 | Meeee (%) | ee (°M) | Mee |
---|---|---|---|
Me | 88 | 888–888 | [888] |
(MM8)Me | 8 | 888–888 | [888] |
(MM8)8Me | 88 | 888–888 | [888] |
MM8=MMMM8 | 88 | 888–888 | [888] |
Me | 88 | 888–888 | [888] |
MM8Me | 88 | 888–888 | [888] |
Meeee 8 Mee Meeeee Meeeeeeeeeeee eeeee Meeee Meeeeeeeee[888]
M8 | e | Meeee (%) | Mee |
---|---|---|---|
M | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
Me | 8 | 88 | [888] |
(MM8)8Me | 8 | 88 | [888] |
Me | 8 | 88e | [888] |
e MeMM, MeMM, ee.
References
[247] | Meeeeeeee, M.; Meeeeeee, M.; Meeee, M., Mee. Meee., (8888) 8, 8888. |
[248] | Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[249] | Meeee, M.; Meeeeeee, M.; Meee, M., Meee. Meeee. Meee., (8888) 88, 8888. |