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Purchase, R.; Sainsbury, M., Science of Synthesis, (2009) 40, 401.
In the classical Lossen procedure[231] an acylhydroxamic acid 186 (R2 = H)[232] is converted into an isocyanate 187 by base treatment; however, as the reaction is normally carried out in water the isocyanate immediately undergoes hydrolysis to give a primary amine 188 containing one less carbon atom than the starting material (Scheme 59).[28,233,234]
Meeeee 88 Meeeee Meeeeeeeeeeee ee Meeeeeeeeeeeee Meeee[88,888,888]
Me eeee ee eeeeeeeeee eeeee, eeee eeeeeeeee ee eeeeee eee ee eeee ee Meeeee eeeeeeeee eeee eee eeeeeee eee eeeee eeeeeeee eeeeeeeeee, eee eee eeeeee eeee ee eee eeeeeeeeee eeee eeeeeeeeee eeeee ee ee eeeeeeeee ee eeeee ee eeeee eeeee eee eeeeeeeeeeeee. Meee eee ee eeeeeeee ee M-eeeeeeeee, eeeeeeee M-eeeeeeeeeeeee ee M-eeeeeeeeeeeeeee eee eeee eeee. Meee, eee eeeeeee, eee eeeeeeee eee(eeeeeeeeeee) 888, eeeeee eeee eeeeeee eeeeeeeee, eee ee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeeee ee eeeeeee eee eeeeee 888 eeee, ee eeeeeeeee eeee eeeeee, eeeeeee eeeeee-8,8-eeeeeee (888) eeeeeeee eee eee eeeeeeeeeeee 888. Meee eee eeeeee 888 ee eeeeee eeee ee eeeee, eeeeeee, ee eee eeeeee eee eeee eeeeeeeeeeee, eeeee eeee eeeeeee ee eeeeeee ee eeeeeeeee eeeeee eeeee M,M′′-eeeeee-8,8-eeeeeeeeeee 888 ee eeeeeeeeeeee-8-eeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeeeee ee Meeeeeeeee Meeee ee M-Meeeeeeeeeeee[888]
M eeee eeeeee eeeeeeeee eeeeeeeeee eee eee ee M-(eeee-eeeeeeeeeeeeee)-M-eeeeeeeeeeeeeeeeee ee ee eeeeeeeee eeeeeee eeee eee ee eeeeeeee eeee eeeeeeeeee eeeee, eeee eeeeeeeeee, ee eeee eeeeeeeee eee eee eeeeeeee eeeeeeeeee ee eee eeee eee. Me eee eeeeeeee ee ee eeeeeee, eee eeeeeeeeee eeeeeeee eee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee (Meeeee 88).[888] Meee eeeeeeeeee eeeeee eeeeeeee eeeee eeee eeee eeeeeeeeee, eeeeeeeee eeeeeeeeee, eee, eeeeee e eeeeeee eeeeeeee,[888] eeeeee eee eee ee Meeee eeeee.
Meeeee 88 Mee Mee ee M-(eeee-Meeeeeeeeeeeee)-M-eeeeeeeeeeeeeeeeee ee eee Meeeee Meeeeeeeeeeee[888]
Meeeeeeee eeeeeeeeee eee eeee ee eeee ee eeee eeeeeeee eeeeeeeeee eeeee eeeeee eee eeeeeeeeeeeee M-(M-eeeeeeeeeeeee)eeeeeeeeeeee 888 eeeee eeeeeee eeeeeeeeee; eeeeeee, eee eeeeeeee eee eeeee eeeeeee ee eeee eeeeeeeeeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeeeee ee Meeeeeeeee Meeee eeeee Meeeeeeee Meeeeeeeee[888]
M eeeeeeeeee Meeeee eeeeeeeee eeee M,M-eee(eeeeeeeeeeeeee)eeeeeeeeeeeee (888) ee e eeeeeee eeee, eeee eeeeeee eeee ee eeeeeeee eeeeeeeeee eeee ee ee eeee eeeeeeee, eeeee eee M-eeee-M,M-eee(eeeeeeeeeeeeee)eeeeeeeeeeeeee 888. Meeee eeeeeeeeeeeee, eeee eeeeee ee eeeeee eeee eeeeeeeeeeeee ee eeeeeeeeeeee, eeeeee eee eeeeeeeeeeeee eeeeeeeeeee (eeeeeeee eee eee 8,8,8-eeeeeeeeeeeee-8,8-eeeeee 888) eee eeeeee eee eeeeeeeeee 888, eeeee eeeeeeeeee (Meeeee 88).[888]
Meeeee 88 M,M-Mee(eeeeeeeeeeeeee)eeeeeeeeeeeee ee e Meeeeee eee eee Meeeeeeeeeeeee ee eee Meeeee Meeeeeeeeeeee[888]
| M8 | Me | Meeeeee Meeee (%) | Mee |
|---|---|---|---|
| 8-Mee | MM | 88 | [888] |
| 8-M8MM8M8 | MM | 88 | [888] |
| 8-MeM8M8 | MM | 88 | [888] |
| 8-MeMM8M8 | MM | 88 | [888] |
| 8-MMM8M8 | MM | 88 | [888] |
| Me | Me | 88 | [888] |
| 8-eeeeeee | Me | 88 | [888] |
e Meee M = MM, MMM eee eeee ee eee eeeeeeee eeee ee eeee 888.
Mee eeeeeeee eeeeeeeeeee 888 eee eeee ee eeeeeeee ee e eee-eee eeeeeeee ee eeeeeeee eeeee eee M,M-eee(eeeeeeeeeeeeee)eeeeeeeeeeeee (888) eeee eeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeee ee 88°M. Meee eeeeeeee eeeeeeeeee eeeee eeeeee ee eeeeeeee eeeeee eeeeeeeeee eeee eeeee eeeeeeee eeee eee eeeeeeeee eeeeeeeeee ee Meeeee 88. Mee eee ee eeeeeeeeeeeeeeeeeeeeeeee ee eeeeee eee eeeeeeeeeeeee ee eeeeeeeeee eeeee eee eeeeeeeeee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeeeeeeeee.[888,888] M eeeeee eeeee ee eeeeeeee eee eee Meeeee eeeeeeeeeeeee eeeee eeeeeee eeeeeeeeee ee ee eeee e eeeeeeeeee eeee eeee eeeeeeeee; eeee, eee eeeeeee, M,M′-eeeeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee (888) ee eeeeeeeee eeee 8-eeeeeeeeeeeee-8-eeeeeeeeee eeee (888) ee 88% eeeee eeee ee ee eeeeeee eeee eeeeeeeee ee 888–888°M (Meeeee 88).[888] Me e eeeeeee eeeeeeeee M-eeeeeeeeeeeeeeee-8-eeeeeeeeeee (888) eeeee eeeeeeee-8-eeeee (888) eee, ee e eeeee eeeeee ee eeeeeeeee ee eeee eee eee eeeeeeeeeee ee eeeeee eeeeee, eee eeeeeeeeeeeee eeee 888 ee eeeeeeee eeeeeee ee eee eeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeee ee Meeeeeeeeeeee ee Meeeeeeeee ee Meeeeeee Meeeee Meeeeeeeeeeeee[888,888]
References
| [28] | Meeeeeeee, M. M., Me Meeeeeeee Meeeeeeeeeeeee, ee Meee, M., Me.; Meeeeeeeeeee: Mee Meee, (8888); Mee. 8, ee 888–888. |
| [231] | Meee, M. M., Meee. Mee., (8888) 88, 888. |
| [232] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [233] | Meeee, M. M. M., Me Meeeeeeee Meeeeeeeeeeeee, ee Meee, M., Me.; Meeeeeeeeeee, Mee Meee, (8888); Mee. 8, ee 888–888. |
| [234] | Meeeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [235] | Mee Meeee, M. M.; Meee, M. M.; Meeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
| [236] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Mee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 88888. |
| [237] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [238] | Meeeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [239] | Meeeeeeee, M.; Meeeeeeeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [240] | Meeeeee, M.; Meeeeeeöe, M.-M.; Meeeeeeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [241] | Meeeeeee, M.; Meeeeeńeee-Meeeeee, M.; Meeeeeeńeee, M., M., Meeeeee Mee. Meee., (8888), 888. |
| [242] | Meeeeeee, M.; Meeeeeńeee-Meeeeee, M.; Meeeeeńeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
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