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Brigas, A. F., Science of Synthesis, (2004) 13, 905.
The Dimroth rearrangement is one of the most general heterocyclic rearrangements. In the field of tetrazole chemistry, it involves the interchange of R1 and R2 in tetrazoles 93, via azidoamidines (Scheme 67). Theoretical studies suggest that the rate-determining step is not the tetrazole ring opening, but it may either be the amidine rotation or the shift of the proton.[2,238,239] The conversion is brought about simply by heating.
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| M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|
| Me | M | MMMM, 888–888°M, 8.8 e | 88 | [888] |
| Me | Me | eeeeee, eeee, 88 eee | 88 | [888] |
| 8-MeM8M8 | M | MMMM, 888–888°M, 8.8 e | 88 | [888] |
| 8-eeeeeeeeeeeeee-8-ee | M | eeeeee, eeee, 88 eee | 88 | [888] |
| 8-eeeeeeeeeeeeee-8-ee | M | eeeeee, eeee, 8 e | 88 | [888] |
| 8-eeeeeeeeeeeeee-8-ee | M | eeeeee, eeee, 88 eee | 88 | [888] |
| 8-eeeeeeeeeeeeee-8-ee | M | eeeeee, eeee, 88 eee | 88 | [888] |
| 8-eeeeeeeeeeeeeeeeee-8-ee | M | eeeeee, eeee, 88 eee | 88 | [888] |
| 8-MeMM8M8 | M | MMMM, 888–888°M, 8 e | 88 | [888] |
| 8-eeeee-8-eeeee | M | eeeeee, eeee, 88 eee | 88 | [888] |
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References
| [2] | Meeeeeeee, M., M. Meeee. Meee./Meee.-Mee., (8888) 888, 888. |
| [75] | Meeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meee, M.; Meeee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [218] | Meeeee, M. M.; Meeee, M.; Meeeee, M. M.; Meeeeee, M. M. M.; Meeeeeeee, M. M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [238] | Meeeeeeee, M.; Meee, M. M.; Meee, M., Meee. Mee., (8888) 888, 8888. |
| [239] | M'eeeé, M.; Meeeeeeeeeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meee. Mee. Meee. Meee., (8888) 88, 888. |
| [240] | Me Meeeeee, M.; Meeeee, M. M.; Meeeeeeeee, M.; Me Meeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeee, M.; Me Meeee, M.; Meeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [241] | Meeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeee. Meee., (8888) 888, 888. |
| [242] | Meeeeeeee, M. M.; Meeeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
| [277] | Meeeee, M.; Meeeee, M.; Meeee, M.M., M. Mee. Meee., (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) 88/8, 888.
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