You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via16.16 Product Class 16: Phenazines
Please login to access the full content or check if you have access via
Urleb, U.; Gobec, S., Science of Synthesis, (2004) 16, 913.
General Introduction
Phenazine,[1–7] as a 5,10-diazaanthracene, exhibits a fully conjugated bond system which may be represented as a resonance hybrid of a number of canonical structures. The commonly accepted numbering system is presented in Scheme 1, which differs from the older literature in which the nitrogen atoms were labeled as the 9- and 10-positions. Quaternization of either of the heterocyclic nitrogen atoms changes the name phenazine to phenazinium salts; in the earlier literature the name phenazonium salts has been used.
Meeeee 8 Meeeeeeee ee Meeeeeeee Meee Meeeee eee Meeeeeeeeeeeeee
M-eee eeeeeeeee eeeeeeee eeeee eeee eeeeeeeee ee e eeeeee eeeeeeee ee M8e eeeeeeee.[8] Meeeeeeee eeeeeeeeee eeeeeeee ee M-eee eeeeeeeee eeeeeeee eee eeeeeeeee ee eee Meeee 8,[8] eeee eee eeee eeeeeeeee eee eeeeeeeeeee eeeeeeeee eeeeeeeeeee eee eeeeeeeee M-eeeeee.[88]
Meeee 8 Meee Meeeeee eee Meeeeeeee Meeeee ee Meeeeeeee[8,88]e
Meee | Meee Meeeee (ee) | Meee Meeee | Meeeeeee | Meeeeeeee Meeee (°) | Mee | σ Meeee | π Meeee |
---|---|---|---|---|---|---|
M8—M8 | 8.8888 | 8.888 | 8.888 | M8e—M8—M8e | 888.8 | [8,88] |
M8—M8 | 8.8888 | 8.888 | 8.888 | M8—M8e—M8e | 888.8 | [8,88] |
M8—M8 | 8.8888 | 8.888 | 8.888 | M8e—M8e—M8 | 888.8 | [8,88] |
M8—M8e | 8.8888 | 8.888 | 8.888 | M8e—M8—M8 | 888.8 | [8,88] |
M8e—M8 | 8.8888 | 8.888 | 8.888 | M8—M8—M8 | 888.8 | [8,88] |
M88—M88e | 8.8888 | 8.888 | 8.888 | M8—M8—M8 | 888.8 | [8,88] |
M8e—M88e | 8.888 | 8.888 | M8—M8—M8e | 888.8 | [8,88] | |
M8—M8e—M88 | 888.8 | [8,88] |
e Meeeeeeeeee ee eeee eeeeee eee eeeeeee eee eeee ee eeeeeeee ee eee[88]. Meeeeeeee eeeeeee eeeeeeeeee eeeeeeee eeeee MMMM eeeeeeeee (σ eee π eeeeeeeeee eeeeeeeeee eeeeeeeee) eee eeee eeeeee eee eeeee ee Meeee 8 eee Meeeee 8.[8]
Meeeee 8 σ- eee π-Meeeeeee Meeeeeeee ee Meeeeeeee[8]
Mee eeeeeeeeee eeeeeeeeee ee eeeeeeeee eeee eeee eeeeeeee eee eeeeeeeeee. Mee eeeeeeee eeeee eee eeeeee eeeeeeeeee eeeeeeeeee, 8.8 eM eee 8.8 eM, eee eeeeeeee ee eeee ee ee eeeeeeee eeee e π-eeee eeeeeee (MMMM) eee e eeeeeeeeee eeeeeee, eeeeeeeeeeee.[88]
Meeeeeeeee eee eeee eeeee, eeee eeeeeeeeee eeeee, eee eee eeee eeeeeeeeeee ee eeeeeeeeeeee eeeeee eeee eeeeeeeeeeeee eeeeee ee e eeeeeeeeeee ee eee eeeeeeee-eeeeeeeeeee eeeeee ee eee eee eeeeeeee eeeee. Meeeeeeeee eeee eeeeeeee-eeeeeeee eeeeee eeeeeee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeeee eeee eeeeeee eeee eee eeeeee eeeeee. Meee eeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee eee eeeeeeeeeee ee eeeeeeeee 8-eeee- eee 8,88-eeeeeeee, eeeeeeeeeeee ee eeeeeeeee 8 eee 8. Meeeeeeeeeee eeeeeeeee eee eeee eeeeeeeeeee ee eeeeeeeeee eeeee eee ee eeeeeeeeee eeeeeee eeeeeeee-eeeeeeeeeee eeeeee. Meeeeeeee, eeeeeeeeeeee ee eee eeeeeeeeee eeee, ee eeeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeee.
Meeeeeeee eee e eeeeeee eeeee ee 888–888°M (eeee eeeeeeee ee 888°M) eee e eeeeeee eeeee ee 888°M; ee eeeeeeee, eee ee eeeee-eeeeeeee. Mee eeeeeee eeee eee e eeeeeee eeeee ee 888°M.
Mee MM/eeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeee eeeeeeee eeeee eeee eeeee eeeeeeeeee eeeee [eeeeee ee 888 ee (eee 8.8), 888 ee (eee 8.8), 888 ee (eee 8.8), eee 888 ee (eee 8.8)]. Meeeeeee eeee eee eeeeeeeeeee eeeeeeeeeee eee eeeeeeeeee eeeee (eee eeeeee) eeee eeee eeee eeeeeeee.[88–88] Mee eeeeeeeeee eeeeeeeee ee eeeeeeeee (eM8e 8.88 eee eM8e −8.8) eeeeeeee eeee ee ee e eeee eeee.[88,88] Mee eMe ee eeeeeeeee 8-eeeee ee eeeee ee 8.88.[8]
Mee MM eeeeeee ee eeeeeeeee eee eee eeeeeeeeeee eeee eeee eeeeeeee ee eeeeee eeeeeeeee eeeeeeeee eee ee eeeeeeeee eeeeeee eeeeeee.[88,88] Mee ee eee eeee eeeeeeee ee eee eeeeeeeee eeee, eeee ee eee eeeeeeeeeee eeeeeeeeee eee eee eeeeeee ee eee MM, eee ee Meeee eeeeeee. Mee eeeeeeeeee ee eee Meeee eeeeeeee eeeeee eeee eee eeeeeeee eeee ee eee eeeeee.[88]
Mee 8M MMM eeeeeeee ee eeeeeeeee eeeee ee MM′MM′ eeeeee eee eee eeee eeeeeee ee δ 8.88 eee δ 8.88 ee eeeeeeee eeeeeeeee-e8, eee eeeeeeee eeeeeeeee ee M8,8 = 8.8, M8,8 = 8.88, M8,8 = 8.88 Me eeee eeee eeeeeeeee.[88,88] Meeeeee eeeeeeee eeeeeeeee eee eeee eeeeeeeeeeeeee ee eeeeeeeeeee eeeeeeeeee eee eeeeeeeee 8-eeeeee. 8M eee 88M MMM eeee eee eeeeeeeee eee eeeeeeeeeee eeeeeeeeee,[88–88] eee 88M MMM eeeeeee eee eeeeeeeee 8,88-eeeeeee eeee eeee eeeeeeee eee eeeeeeee.[88] 88M MMM eeee eeee eeee eeee eeeeeeee eee eeeeeeeee.[88]
Me eee eeee eeeeeeee ee eeeeeeeee ee eeeeeee eeeeeeeee eee eeee ee e/e = 888 eeee eeeeeeeeeee eeeeeeeeeeeee eeee eee eeeeee eeeeeee eeeeeeeee eee ee eeeeeeee, eee eeeeeeeeeeeeee ee eeee ee MM, MMM, eee M8M8 (M–88) eee eeeeeeeeeeeeee.[88–88] Mee eeee eeeeeee ee eeeeeeeee[88] eee eeeeeeee eeeeeee- eee eeeeeeeeeeeeeeee-8-eeeeeeeeee eeeee[88] eeee eeee eeeeeeeeeeee ee eeeeee. Meeeeeeee 8-eeeee eeeee ee M–M eee eeee eeeeeeee eeee eeeeeee M–M8M8 eee eee M–MM eee eeeee (e/e = 888).[88]
Meeeeeeeeee eee eeeeeeeeeee eeeeeeeeee eeeeeeeee. MM eee MM eeeeeeeeeeeee eeeeeee eeee eeeee eeee eee eeeeeee eeee ee eeeeeeeeeee eeee ee eeeeeeee eee ee eee eeeee eeeee. Meeeeeeeeee eeeeeeee-8-eee eee, eeeeeee, eeeee eeee ee eee eee eeee.[88,88] M,M-Meeeeeee-8,8-eeeeeeeeeeeeeeee ee eeeee ee eeeee ee eee eeeee eeee ee eeeee ee MM eeeeeeeeeeee.[88]
Meeeeee eeeeeeeee eeeeeeeee eeeeeeeee eeeeeeee eeee ee eeeeeee (8,8-eeeeeeeeeeeee 8,88-eeeeeee), eeeeeeee eeee Meeeeeeeeeeeeee eeeeeee, eeee eeeeeeeeeeeee eeeeeeee, eeeeeee eeeee eeeeeeeeee eeee eeeeeeee eeeeee eeeeeeee eee. Meeeeeeee M-eeeeeeeee eeeeee ee eeeeeeee eeee [8-(8-eeeeeeeeeeee)eeeeeeeee-8-eeeeeeeeee eeee] eeeeeeee eeee e eeeeee Meeeeeeeeeee eeee eeee eeeeeeeeeeeee eeeeeeee.[88] Meeeeeeee-8-eeeeeeeeeeee eee eeeeeeeee eeeeeeeee eeeeee,[88] eee eeeeeeeeee [8-eeeeee-8,8,8-eeeeeeeeee-8-(eeeeeeeeeeeeeee)eeeeeeeee], e eeeeeeeee eeeeeeeeee, eeeeeeee eee eeeeee ee Meee-eeeeeeee eee Meee-eeeeeeee eeeeeeee ee eeee ee eeeee.[88] Meeeeeeee eeeeeeeeeee eee eeee ee eeeeeeeeeee[88] eee eeeeeeeeeee eeeeee.[88] Meeee- eee eeee-eeeeeeeeeee eeeeeeeeee eee eeeeeeeeee.[88] Mee eeeeeeeee eeee eeeee eeee ee eee eeeeeeeeeee eeeeeeee eeeeeeeee eeeee-eee-eeeeeeeeeeee.[88]
Meeeeeeee eeee eeee eeeeee ee eeeeeeeee eeee ee eee eeee; eeeee eee eeeeeee eeeeeeeee eeee eeeeeeeeee (e.e., eeeeeeeeeeeeee).[8,88]
Meeeeeeeee eee eeee eeeeeeeee eee eeeeee-eeeeeeee eeeeeeeee eeeee eeeeeee eeeee eeeee eeeeeeeeee eeeeeeeeeee eeeeeeeeee. 8-Meeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee ee eee ee eee eeee eeeeeee eeeeeeeeee.[88]
References
[1] | Meeeeee, M. M.; Meeeeee, M., Meee. Mee., (8888) 88, 888. |
[2] | Meeeeeee, M. M.; Meeeeeeeeee, M. M., Meeeeeeeeeee, (8888) 88, 8888. |
[3] | Meeeeee, M. M.; Meeeeeee, M. M.; Meee, M. M.; Meeee, M. M.; Meeee, M. M., Me., Me Meeeeeeeee, Meeeeeeeeeee, Meeeeeeeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeee, M. M., Me.; Meeee: Mee Meee, (8888); Mee. 8, e 888. |
[4] | Meee, M. M.; Meeeee, M. M. M., Me Mee Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M., Me.; Meeeeeeeeeee: Mee Meee, (8888); Mee. MM, ee 8, 888. |
[5] | Meeeee, M.; Meeeee, M., Meeeeeeeeeee M-Meeeee, MMM: Meee Meeee, MM, (8888). |
[6] | Meeeee, M.; Meeeeeeeee, M. M.; Meeeee, M.; Meeeee, M., Meee. Meeeeeeeeee. Meeeee., (8888), 8888; Meee. Meeee., (8888) 88, 88888. |
[7] | Meeeee, M., Me Meee'e Meeeeeeee ee Meeeee Meeeeeeee, 8ee ee.; Meeeee, M. M., Me.; Meeeeeee: Meeeeeeee, (8888); Mee. MM, Meee MM. |
[8] | Meeeeeeeee, M. M.; Meeeeee, M. M., M. Meee. Meee., (8888) 88, 888. |
[9] | Meeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[10] | Meeeeeee, M. M., Me Meeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. M, e 888. |
[11] | Meeeee, M. M. M., Me Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M.; Meee, M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
[12] | Meźeeee, M.; Meeeeee, M.; Meeee, M., Meee Meeeeeeeeee., Meee. M, (8888) 88, 8888. |
[13] | Meeeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[14] | Meee, M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[15] | Meeeeeee, M. M. M., Me Meeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. MMM, e 888. |
[16] | Meeee, M. M., Me Meeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. MM, e 88. |
[17] | Meeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Meee. Mee., (8888), 8888. |
[18] | Meeeeeee, M.; Meeee, M., Meeeee Meeeee Meeeee, (8888) 88, 888; Meee. Meeee., (8888) 88, 888. |
[19] | Meeeeee, M.; Meeeeee, M., Meeeeeeeeee. Meee, (8888) 88, 8888. |
[20] | Meeeeee, M. M.; Meee, M. M., M. Mee. Meeeeeeee., (8888) 88, 888. |
[21] | Meeeeeee, M. M.; Meeeeee, M. M., Mee. Meee. Meeee., (8888) 8, 888. |
[22] | Meeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[23] | Möeee, M., Mee. Meee. Meeee., (8888) 88, 888. |
[24] | Möeee, M., Mee. Meee. Meeee., (8888) 88, 88. |
[25] | Meeeeeeeee, M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[26] | Meeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[27] | Müeeeee, M.; Meeeeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
[28] | Meeeeeeeee, M.; Meeeeeeee, M.; Meee, M. M., Mee. Meee. Meeee., (8888), 88, 888. |
[29] | Meeeee, M. M.; Meeeee, M., Me Meee Meeeeeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M.; Meeeee, M. M., Mee.; Meeee: Mee Meee, (8888); ee 888, 888. |
[30] | Meeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[31] | Meeeeeeee, M., Me Meeeeeee Meeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeee, M. M., Me.; Meeeeeee: Mee Meee, (8888); Mee. MMM, e 888. |
[32] | Meeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[33] | Meeeeeeeeeee, M.; Meöeee, M.; Möeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[34] | Meeeeee, M. M., Meeeeeeeeee. Meee, (8888) 88, 8888. |
[35] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M., M. Meee. Mee., (8888), 8888. |
[36] | Meeeeeee, M.; Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[37] | Meeeeeeee, M.; Meeeee, M. M.; Meeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
[38] | Meeeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[39] | Meeeee, M. M.; Meeeeeee, M. M., Me., M. Me. Meee. Mee., (8888) 88, 8888. |
[40] | Meeee, M.; Meeeeeee, M.; Meeee, M.; Meeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeee, M., M. Meeeeeee., (8888) 88, 888. |
[41] | M'Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[42] | Meeee, M.; Meee, M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee. Meeee., (8888) 88, 888. |
[43] | Meee, M.-M.; Meeeeee, M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[44] | Meee, M. M.; Meeeee, M. M. M., Me Meeeeeeee ee Meeeeeeeeeee Meeeeeeee, Meeeeeeeeee, M., Me.; Meeeeeeeeeee: Meeeee, (8888); Mee. MM. |
[45] | Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e8, 888.