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Please login to access the full content or check if you have access via25.6.6.10.2 Variation 2: In Situ Generation of Hydrogen Cyanide from 1,3,5-Triazine (Kreutzberger Modification)
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Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 640.
1,3,5-Triazine (39) can be used as a source of hydrogen cyanide; however, yields are generally lower compared to the direct employment of cyanide (Table 18).[130,131] In the presence of hydrogen chloride, electron-rich arenes react with 1,3,5-triazine (39) to give the aldimine hydrochlorides 40, which are hydrolyzed to the corresponding aromatic aldehydes (Scheme 22). Less-activated arenes require stoichiometric amounts of a Lewis acid such as zinc(II) chloride or aluminum trichloride; nevertheless, even toluene can be formylated in good yields under these conditions.
Meeeee 88 Meeeeeeeeeee Meeeeeeee ee eee Meeeeeeeee Meeeeeee[888–888]
Meeee 88 Meeeeeeeeeee Meeeeeeeeeee ee eee Meeeeeeeee Meeeeeeeeee eeee Meeeeee Meeeeeeeeee eee Meeeeeeeee Meeeee[888–888]
| Meeee | Me8 | Meeeee | Meeee (%) | Mee |
|---|---|---|---|---|
| 8 |  |
M | 88 | [888] |
| 8 | |
M | 88 | [888] |
| 8 | |
M | 88 | [888] |
| 8 | |
M | 88 | [888] |
| 8 | 8-MMM8M8 | M | 88 | [888] |
| 8 | 8-MeMM8M8 | M | 88 | [888,888] |
| 8 | 8-MeMM8M8 | M | 88 | [888] |
| 8 | |
M | 88 | [888] |
| 8 | 8,8-(MeM)8M8M8 | M | 88 | [888] |
| 88 | 8,8-(MeM)8M8M8 | M | 88 | [888] |
| 88 | |
M | 88 | [888] |
| 88 88 |
|
M M |
88 88 |
[888] [888] |
| 88 | 8-Mee | M | 88 | [888] |
| 88 | 8,8-Me8M8M8 | M | 88 | [888] |
| 88 | Mee | M | 88 | [888] |
| 88 | |
M | 88 | [888] |
| 88 | |
M | 88 | [888] |
| 88 | |
M | 88 | [888] |
| 88 | |
M | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeeeeeeeeeeeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[888]
Meeeee M: Me e eeee ee eeeeeee-8,8,8-eeeee (8.8 e, 8.88 eee) eee 8,8,8-eeeeeeee (88; 8.8 e, 8.88 eee) ee eeeee Me8M (88 eM) eee eeeeee MMe(e) eee 8 e. Meeeee eeeeeee, eee eeeeeeee eeeeeeeeeeeee eeeeeee ee eeeeeeeeeee. Meeee eee eeeeeeee eeee, eee Me8M eee eeeeeee eee eee eeeeeee eee eeeeee ee M8M (88 eM) eee 88 eee, eeeeeeee ee eeeeeeee ee eeeeeeee eee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee 8,8,8-eeeeeeeeeeeeeeeeeeeeee, eeeee eee eeeeeeeeeeeeee (M8M) ee eeee eeeee eeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.
8-Meeeeeeeeeeeeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.
Me e eeee ee Me8M (88 e, 8.8 eee) eee 8,8,8-eeeeeeee (88; 8 e, 8.88 eee) ee eeeee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeee eeee eeeeeee, eeeeeeee MeMe8 (88.8 e, 8.8 eee). MMe(e) eee eeeeee eeeeeee eee eeee eee 8 e ee 88°M eee eeeeeeeeeeee eee 8 e ee 88–88°M. Mee eeeeeee eee eeee eee 88 e ee ee, eeeeeeeeeeee eeeeeee eeee eeeeeee (88 eM), eeeeee eeee e eeeeeee ee 88% MMe (88 eM) eee eee, eee eeee eeeeeeee eee 88 eee. Meeee eeeeeee ee ee, eee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee Me8MM8 eeee eee M8M, eeeee, eee eeeeeeeee eeeee eeeeeee eeeeeeee (8 Meee) ee eeee eee eeeeeee ee eeeeeeeee eee; eeeee: 88.8 e (88%).
References
| [130] | Meeeeeeeeee, M., Meee. Meeee. Mee. Meeee. Meeee. Mee., (8888) 888, 888. |
| [131] | Meeeeeeeeee, M., Meeee. Meee., (8888) 88, 888; Meeee. Meee. Mee. Me. Meee., (8888) 8, 888. |
| [132] | Meeeeeeeeee, M., Meee. Meeee. Mee. Meeee. Meeee. Mee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 88.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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