You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via41.9.1.4.1 Variation 1: Diazotization of Arylamines and Reaction with Secondary Amines
Please login to access the full content or check if you have access via
DOI:
10.1055/sos-SD-041-00570
Jung, N.; Bräse, S., Science of Synthesis, (2010) 41, 619.
Arenediazonium ions (e.g., 20) react with secondary amines in aqueous solution or other solvents to give 3,3-dialkyl-1-aryltriazenes (e.g., 21) (Scheme 8) or 3-alkyl-1,3-diaryltriazenes. Reaction of other diazonium ions (Table 1) with amines can also be used to synthesize 3-alkyl-1,3-dihetaryltriazenes.
Meeeeeee eeeeeee eee eee eeeeeeeeeeeee ee eeeeeeeeeeeeeeee eeee eee eeee eeeee ee Meeeeee ee Meeeeeeee, Mee. 88e [Meeee—M (M = M, M) (Meeeeee 88.8888.88)] eee Meeeee–Meee Mee. M 88e/8, e 8888ee eee eeeeeeeeee eeeee eeeeeee.
Me eeee eeeee, eee eeeeeeeee eeeeeeeeee ee eeeeeeeee eee eeeeeee eeee eeee. Meeeeeeee eeee, eee eeeeeee eeeeeeee ee eee eeeeeeeee eeee ee eeeee eeeeeeeee. Meeee eeeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeeee ee eeeeeeee eeee eee eeeeeee eeeeeeee, eeeeeeeeeeee eee ee eeeeeeeee ee eeeeeeeeeeeeeee, eeeeeeeeeeee, ee eeeeeeeeeeeeee. Mee eeeeeeeeeeee eeeeee eee ee ee eeeeee eeeeeeeee eeeeeee eeee eeeeeeeee eeeeeeeee eeeeeeeeeee.
Meeeee 8 Meeeeeeee eeee Meeeeeeee Meeee eee Meeeeeeeeeee[88]
Meeee 8 Meeeeeeee eeee Meeeeeeee Meeee eee Meeeeeeee Meeeee[88,88–888]
| Meeeeeeee Mee | Meeee | Mee |
|---|---|---|
| eeeeeeeeeeeeeeee eeee | Me8MM | [88–88] |
| Me8MM | [88–88] | |
| MeMMMe | [88,888] | |
| MeM8MMM8MMMe, MM(MM8)8MMMe, MeM8M(MM8)8MMMe, Me8MM | [88] | |
| Me8MM, Me(MM8)8MMMe, (M8M=MMMM8)8MM, M8M=MMMM8MMMe, eeeeeeeee, MeMM(MM8)8MMMe | [88] | |
| 8-MeM8M8MMM8 (M8 = Me, Me, MM8MM=MM8, Me, Me) | [88] | |
| eeeeeeee | [88] | |
| eeeeeeeeeee, eeeeeeeeee, eeeeeeeeee, Me8MM, Me8MM | [88] | |
 |
[88] | |
| Me8MM, 8-(MeMMMM8)M8M8(MM8)8MeM8e+8 | [88] | |
| MeMMMe, MeM(MM8)8MMMe, MM(MM8)8MMMe | [88] | |
| MeMMMe, MeMMMe, MeMMMe, MeMMMe, MeMM(MM8)8Me, MeMMeMe, MeMMe-Me, MeMMMe | [88] | |
| MeMMMM8MM8e-Me | [88] | |
| eeeeeeee, eeeeeeeeeeee | [88] | |
| (MMMM8MM8)8MM, eMe8MM, Me8MM, e-Me8MM, Me(MM8)8MM, (eMeMM8MM8)8MM, [eMe(MM8)8]8MM, Me(MM8)8MM, Me8MM, eeeeeeeeeee, MeMMMe, MeMMMe, 8,8,8,8-eeeeeeeeeeeeeeeeeee, 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee | [88] | |
| eeeeeeeeee, eeeeeeeeeee, eeeeeeeeee, 8,8-eeeeeeeeeeeeeeeeee, MMM, 8-eeeeeeeeeeeeeeee, 8-eeeeeeeeeeeeeeee, 8-eeeeeeeeeeeeeeee, eeeeeeeee-8-eee, eeeeeeeee-8-ee, eeeeeeeee-8-ee, eeeeeeeee-8-eee, 8,8,8,8-eeeeeeeeeeeeeeeeee, 8,8,8,8-eeeeeeeeeeeeeeeeee, eeeeeeeeee-8-eee, eeeeeeeee-8-ee, eeeeeeeee-8-ee, eeeeeeeee-8M-eeeeeee | [88,88] | |
| Me8MM | [88,888] | |
| 8-eeeeeeeeeeeeeeee, eeeeeeeeeeee: 8,8-eeeeeeeee, eeeeeeeeee, 8-eeeeeeeeeeeeeeee | [88,88] | |
| MeMMMM | [88] | |
| Me8MM, MeM(MM8)8MMMe | [88] | |
| eeeeeeeeeeee | [88] | |
| Me8MM, eeeeeeeeee, eeeeeeeeeee | [88] | |
| eeeeeeeeeeeeeeee eeee (eeeee-eeeee eeeeeeee) | eeeeeeeeeeee | [88] |
| Me8MM | [88,888–888] | |
| eeeeeeeeee, eeeeeeeeee, eeeeeeeee-8-ee | [888] | |
| eeeeeeeeeee | [888] | |
| MeMMMe | [888] | |
| Me8MM | [888] | |
| |
[888–888] | |
| |
Me8MM, Me8MM, eMeMMMe, Me8MM, [Me(MM8)8]8MM, MeMMMe, eeeeeeeeeee, eeeeeeeeee | [888] |
| |
Me8MM, eMeMMMe, MeMMMe, MeMMMe, Me(MM8)8MMMe, MeMMMe, MM(MM8)8MMMe, MMMM8MMMe, eeeeeeeeee, eeeeeeeeeee, Me8MM, [Me(MM8)8]8MM, eMe8MM, Me8MM, MeMMMe, MeMMMM8(MMMM)8MM8MM | [888] |
| |
Me8MM, Me8MM, MeMMMe, eeeeeeeeeee | [888–888] |
| |
(MeMM8MM8)8MM, (MMM8MM8)8MM | [888] |
| |
eeeeeeeeeee, Me8MM, Me8MM | [888] |
| |
Me8MM, Me8MM, (MMMM8MM8)8MM, MM(MM8)8MMMe, (MMM8MM8)8MM, (MeMM8MM8)8MM | [888,888] |
| |
Me8MM | [888–888] |
| |
Me8MM | [888] |
| |
Me8MM, eeeeeeeeee | [888] |
| |
(MMM8MM8)8MM, MeMMMe, (MMMM8MM8)8MM, (MeMM8MM8)8MM | [888–888] |
| |
Me8MM, Me8MM | [888] |
| |
Me8MM, Me8MM | [888] |
| |
Me8MM, Me8MM, eeeeeeeeeee | [888] |
| |
Me8MM, MeMMMe, M8M=MMMM8MMMe, MeMMMe, Me(MM8)8MMMe, MM(MM8)8MMMe | [888] |
| |
Me8MM, MeMMMe, Me8MM, Me8MM, MeMMMe | [888] |
| |
Me8MM | [888] |
| |
Me8MM | [888] |
| |
(MMMM8MM8)8MM, MM(MM8)8MMMe, MM(MM8)8MMeMe, MM(MM8)8MMMe | [888] |
| |
Me8MM | [888] |
| |
Me8MM, Me8MM, eeeeeeeee-8M-eeeeeee | [888] |
| |
Me8MM, eeeeeeeeeee, eeeeeeeeee, Me8MM | [888] |
| |
Me8MM, Me8MM | [888] |
| M-(eeeeeeeeeeeeeeeee)-M-eeeeeeeeeeeeee | [888] | |
| |
Me8MM, eMe8MM | [888] |
| |
eeeeeeeeeee, Me8MM | [888] |
| |
Me8MM | [888] |
| |
Me8MM, eeeeeeeeeee, eeeeeeeeee, Me8MM | [888] |
| |
eeeeeeeeee, 8-eeeeeeeeeeeeeeee, Me8MM | [888] |
| |
eeeeeeeeeee, Me8MM, Me8MM | [888] |
| |
eeeeeeeeeee, Me8MM, Me8MM | [888] |
| |
Me8MM | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meee-8,8-eeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
M eeee ee MeMM8 (8.8 e, 8.888 eee) ee M8M (88 eM) eee eeeee eeeeeeee ee 8°M ee eee eeeeeeeee 88 (8.8 eee) ee eeeee MMe (88 eM) eee M8M (88 eM). Mee eeeeeee eee eeeeeee eee 88 eee ee 8°M eee eeee eeeee ee e eeee ee M8MM8 (88.8 e, 8.88 eee) eee Me8MM (88.8 e) ee eee eeeee (888 eM). Mee eeeeeee eee eeeeeeeee eeeeeee eeeee eeee Me8M eee eee eeeeeee eeeeee eeee eeeeee eeee M8M eee eeeee (MeMM8). Meeee eeeeeee ee eee eeeeeee, eee eeeee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee.
References
| [28] | Meäee, M.; Meeeee, M.; Meeeeeeeeeee, M.; Meeeeeeeee, M. M.; Meeee, M. M., Meeeee. Mee. Meee. Meee., (8888) 88, 8888. |
| [50] | Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeee Meeeeeeee Meeeee, (8888) 88, 888; Meee. Meeee., (8888) 88, 888888. |
| [52] | Me, M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [53] | Meeeeee, M. M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeee, M.; Meee, M. M. M., Meeeeee. Meeeeeeee., (8888) 88, 8888. |
| [54] | Meeee, M.; Meeeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
| [55] | Meeeee, M. M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [56] | Meeeeee, M.; Meee, M.; Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [57] | Meeeeeeee, M. M.; Meeeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [58] | Mee, M.; Meeee, M.; Mee, M., Meeee Meeeee, (8888) 88, 888; Meee. Meeee., (8888) 888, 88888. |
| [59] | Meeee, M. M.; MeMeeeeeee, M. M., M. Meee. Mee., Meeee., (8888) 8, 888. |
| [60] | Meeeeee, M.; Meeee, M.; Meeeeee, M.; Meeeee, M., Meeee-Meee. Meee., (8888) 88, 88; Meee. Meeee., (8888) 88, 88888. |
| [61] | Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeee, M.; Meeee, M.; Meeeeeeee-Meeee, M., Mee. Meee. Meee., (8888) 88, 888. |
| [62] | Meeeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeee, M., Meeeeee. Meeeeeeeee., (8888) 88, 88; Meee. Meeee., (8888) 88, 888888. |
| [63] | Meee, M. M., MMM; Meeeeeeee, M. M., M. Meeee. Mee., (8888) 88, 8888. |
| [64] | Meeeee, M.; Meeeeeee, M.; Meee, M.; Meeee, M., Mee. Meee. Meeeee. Mee., (8888) 88, 888. |
| [65] | Meeeeeee, M.; Meee, M.; Meeeeeee, M.; Meee, M.; Meeeeeee, M.; Meeee, M., Meeeeee.-Meeeee., (8888) 88, 8888. |
| [66] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeeeee, M. M., Meeee. Meee. M., (8888) 88, 888. |
| [67] | Meeeeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeee, (8888), 8888. |
| [68] | Meeeáeee-Meeeee, M.; Meeee-Meeíe, M.; Meeeeee-Meeeíeeee, M.; Meeeeee, M., Meeeeee, (8888), 8888. |
| [69] | Mee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [70] | Meeeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [71] | Meeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [72] | Meeeeee, M. M.; Meeeeee, M. M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [73] | Meee, M. M.; Meeee, M. M., Mee. Meee., (8888) 8, 8888. |
| [74] | Mee, M.; Meeeöeeee, M.; Meäee, M., M. Meee. Meee., (8888) 8, 88. |
| [75] | Meee, M.; Meee, M.; Meeeee, M.; Meeee, M. M.; Meee, M.; Meeeeeee, M.; Meee, M. M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [76] | Meeeeee, M.; Meee, M., Mee. Meee., (8888) 8, 8888. |
| [77] | Meeeeee, M.; Meee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [78] | Meeeeee, M. M.; Meeee, M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [79] | Me, M.; Meee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [80] | Meeeee, M.; Meeee, M., Mee. Meee., (8888) 8, 888. |
| [81] | Meeeee, M.; Meeeeeee, M.; Mee, M.; Meeeeee, M., Me. Meee., Mee. M, (8888) 88, 88. |
| [82] | Meeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeeeee, M.; Máeeáeee, M., M. Mee. Meeeee., (8888) 88, 888. |
| [83] | Meeeeee, M. M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [84] | Meeeeeee, M. M.; Meeeeeee, M.; Meeeeee, M. M.; Meeee-Meeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [85] | Meee, M. M.; Meeeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [86] | Meee, M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [87] | Meeeee, M. M.; Meeeeeeee, M.; Meeeee, M.; Meeeeeeeeeee, M.-M.; Meeee, M., Meee. Meee. Meee, (8888) 88, 888. |
| [88] | Meeeee, M.; Meeeee, M.; Meeeeee, M., M. Meee. Mee. Meee., (8888) 88, 888. |
| [89] | Meeeeeee, M.; Meee, M.; Meeee, M.; Meee, M.; Meeeeee, M., M. Meeee. Mee., (8888) 88, 8888. |
| [90] | MeMeeeee, M. M.;Meeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [91] | Meeeeeeeeee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [92] | Meeeeee, M.; Meeeeeee, M. M.; Meeeeee, M. M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [93] | Meeeeee, M.; Meeeeee, M. M. M.; Meeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [94] | Meeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [95] | Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [96] | Meeeee, M. M.; Meeee, M. M.; Meeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [97] | Meee, M. M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M. M., M. Mee. Meee., (8888) 88, 8888. |
| [98] | Meeeeee, M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., Mee. M. Meee., (8888) 88, 8888. |
| [99] | Meeeeeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M.; Meee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
| [100] | Meeeeee, M. M. M.; Meeeee, M. M., Me-Meeee, M.; Meäee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888. |
| [101] | Meeeeee, M.; Meeeeeeeeeee, M.; Meäee, M., Mee. M. Mee. Meee., (8888), 8888. |
| [102] | Meeeeeeeee, M.; Meäee, M., M. Meee. Meee., (8888) 8, 8888. |
| [103] | Mee, M.; Meäee, M., Meee.–Mee. M., (8888) 88, 8888. |
| [104] | Meeee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 888. |
| [105] | Meeeee, M.; Meeeeee, M.; Meeeee-Möeeeeeeee, M.; Meeeeee, M.; Möeeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [106] | Me, M.; Meee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [107] | Meeeeee, M. M.; Mee, M. M.; Meeee, M.; Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [108] | Meeee, M.-M.; Meee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
| [109] | Me, M.; Meeeeeee, M.; Me, M.; Meee, M.; Meee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [110] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [111] | Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., Me., M. Meeee. Mee., (8888) 88, 8888. |
| [112] | Meeeee, M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [113] | Meeeeeeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeee Meeeee., (8888) 88, 88. |
| [114] | Meeeee, M. M.; Meeeee, M. M., Meeeee (Meeeee), (8888) 888, 888. |
| [115] | Meee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [116] | Meeeee, M. M.; M’Meee, M. M., M. Meeee. Mee., (8888) 88, 8888. |
| [117] | Meeeeeee, M. M.; Meeeee, M.; Mee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [118] | Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M., Meeee. Meee. M., (8888) 88, 888. |
| [119] | Meeeee, M. M.; M’Meee, M. M., M. Meeee. Mee., (8888) 88, 888. |
| [120] | Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [121] | Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M., Meeeeee, (8888) 88, 888. |
| [122] | Meeeee, M. M.; M’Meee, M. M., M. Meeee. Mee., (8888) 88, 888. |
| [123] | Meeeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeeeeee, M., Mee. M. Mee. Meee., (8888) 88, 888. |
| [124] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M., Meeeeee. Meee., (8888) 888, 8888. |
| [125] | Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [126] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [127] | Meeeee, M. M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [128] | Meeeee, M.; Meeee, M.; Meeeeeeee, M., M. Meeeeeeeeee., M, (8888) 88, 888. |
| [129] | Meeeeeeeee, M.; eee Meeeeeeee, M.; Meeee, M., Meeeeee. Meeeeeeee., (8888) 88, 8. |
| [130] | Meeeeee, M.; Meeeee, M.; Meeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [131] | Meee, M.; Meeeeee, M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [132] | Meeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [133] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Müeeee, M., Meeeeeeee, (8888), 8888. |
| [134] | Mee, M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [135] | Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeeeee, M. M., Meee.-Meee. Me., (8888) 88, 88; Meeee. Meee. M., (8888) 88, 888. |
| [136] | Meeeeeeeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M. M., Mee. M. Mee. Meee., (8888) 88, 888. |
| [137] | Meeeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeeeee, M. M.; Meeeeee, M.; Meeeeeeeeee, M., Meeeeeeeee Mee., (8888) 88, 888. |
| [138] | Meeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meee, M.; Meee-Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Return to Top