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Purchase, R.; Sainsbury, M., Science of Synthesis, (2009) 40, 382.
Anionic [3,3]-sigmatropic rearrangements of N-acyl-N′-phenylhydrazines are known to afford (2-aminophenyl)acetamides, but these products may be mixed with compounds formed by competing Sommelet–Hauser-type and Stevens-type migrations.[90] The acid-catalyzed [5,5′]-sigmatropic rearrangement of hydrazobenzenes that gives 4,4′-diarylbiaryls is commonly known as the benzidine rearrangement. This reaction is well covered in the older literature and, more recently, is summarized in at least two papers[91,92] as well as in Science of Synthesis, Vol. 31b [Arene—X (X = N, P) (Section 31.28.1.33.3)]. As a result further discussion in this section is unnecessary, although it is observed that N,N′-diarylhydrazides 97 tethered with a polyether group at the meta positions undergo the rearrangement to afford benzidines 98 strapped by a polyether unit at the 2,2′-positions (Scheme 27).[92]
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References
| [90] | Meee, M.; Meeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [91] | Meee, M.-M.; Mee, M.-M.; Meee, M.-M.; Mee, M.-M.; Mee, M.-M., Mee. Meee., (8888) 8, 8888. |
| [92] | Mee, M.-M.; Mee, M.-M.; Meee, M.-M.; Mee, M.-M., Mee. Meee., (8888) 8, 8888. |
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- 8.Meeeee-Meee, (8888) 88/8, 888.
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