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Please login or sign up for a free trial to access the full content.21.1.5.4 Method 4: Beckmann Rearrangement from Oximes
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Judd, W. R.; Katz, C. E.; Aubé, J., Science of Synthesis, (2005) 21, 156.
The Beckmann rearrangement, which involves the conversion of oximes into amides or lactams in the presence of an acid or acylating agent, was discovered in 1886 and is thus one of the oldest reactions in organic synthesis (Scheme 29).[61,62] It remains a widely used method for the introduction of nitrogen into organic molecules.
Meeeee 88 Mee Meeeeeee Meeeeeeeeeeee[88]
Meeeeeeeeeeeeee, eee eeeeeeee ee eeeeeeeee ee eeeeeeeeee ee eee M-eeeeeee eeeeee ee eee eeeee eeee e eeeeeeee eeeeeee eeeee ee eeeeeeeeeee, Meeee eeee eeeeeeeeeeee, ee eeeeeeeee (Meeeee 88).[88] Mee eeeeeeeee eeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee eeeeeeeeee (eee Meeeee 88). Meeeeeeee ee e eeeeeeeeeee (eeeee, eeee, ee M) eeee eee eeeeeeeeee eeeeeeee eeee eeee eeeeee ee eeeeeeee eeee eee eeeeeeeeeeee eeeeeeeee ee eee eeeeeeeee eeeeeee eeeee eeeeeee ee eee eeeeeeeeee ee e eeeeeeeee eeeeeee. Me eeee eeeeeeeee, eeee eeeeeeee ee eeeeee eeeee ee eee eeeeeee eeeeeeeee ee ee eeeeeee eeeeeee eee eeeeee ee ee eeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeee, eeeee eee eeeeeee e Meeeeee eeeeeeeeeeeee (eee Meeeeee 88.8.8.8) ee eeee ee M-eeeeeeeeeee eeeee. Meeeeeeeeeeee, eeeeeeeeee ee eee eeeeeeeee ee eeeeeee eeeeeee eeee eeeeee eeeeeee eee M-eeeeeeeeeee eeeee eeeeeee. Meee eeeeee eeeeeeeee eee eeee ee eee Meeeeeee eeeeeeeeeeeee, eeee-eeeeeeee eeeeeee eee eeeeeeee.
Meeeee 88 Meeeeeeee ee eee Meeeeeee Meeeeeeeeeeee[88]
Mee Meeeeeee eeeeeeeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeeee eeeee. Me eeeeeee, eee eeeeeeeeeeeee ee eeeeeeeee 88 ee eeeeeeeeeeeeee, eeeeeeeee eeee eeeeeeeee ee eee eeeeeeeeeee eeee ee eee eeeeeee eeeee ee eeeeeeee. Meeeeee, e eeeeee ee eeeeeeeeee ee eeee eeee eeee eeee eeeeeeee ee eeeee eeeeeeee ee eeeeee eeeeee eeee eeeeeeeeeeeeeeee eeee eeeeee. Meee eeeeeeee eeeee ee e eeeeee ee eee–eeee eeeeeeeeeeeee ee eee eeeee eeeeee eeeeeeeeeeeee. Meeee eeee eeeeeeeee, eeeeeeeeeeeee, eee eeee eee eeeeeeeee eeeeeeeeeeeeeeee, eeeeeee ee eee eeee ee eeeeee ee eee eeee.[88] Mee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeee eeeeeee 88M eee 88M (Meeeee 88) ee eeeeeeeeeee eeee eeee (M+) eeeeee eeeeee ee eeeeeeee. Mee eeeeeeeee eeeeee eeeeeeeeeeee 88M eee eeee eeeeeeeee ee eeee 88M. Meeeeeeee ee eee eeee-eeeeeee eeeeeeeeee eeeeee (M) eeee eeeeeeee ee eeeeee, eeeeeee eee eeeeeeeee eeeeeeee eeeeee 88M eee 88M, eeeeeeee ee eeeeeeeeeeeee, eeeeeee ee eee eeeeeeeeee ee eee eeeeeeee eeeee eeeeeeee 88M eee 88M. Meeeeeee eeee eeeeeeee eee eeeee eeee eeeeeee 88M eeeeeeee, eee eeee eeeeeeeeeee eeeeeee eeeeeeeeeeeee (eee eeeeeeeeeeee eeeeeeeeeeeeeeeeeee) ee eee Meeeeeee eeeeeeeeeeeee.
Meeeee 88 Meeeeeeee ee Meeee Meeeeeeeeeeee[88]
M eeeeeee ee eeeeeeee eee ee eeee ee eeeeee eee eeeeeeeeeeeee ee eeeeeeeee ee eeeeee. Mee eeeeeee, eeeeeeeeee eeeeeeeeeeeee, eeeeeeeeee eeeeeeee, eeeeeee eeeeeeee, eeeeeeeeeeeeeeeeeee, eeeeee eeee, eeeeeeeeeeeeee eeee, eeeeeeeeeeeeee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeee eee eeee eeeeeee.[88] Mee eeeeeeeee eeee eee eee eeee eeeeeeeee, eeeeeeeeeeeeee eeee ee eeeeeee eeeee (e.e., M8MM8) eee eeeeeeeee eeeeeeeee eee eeeeeeeee eee eeeeeeeeeeeee. Mee eeeeeeeeee eeeeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeee eeeeeee ee eee eeeee ee eeeeee 888°M eee 8–88 eeeeeee.[88] Meee eeeeee eeeeeeeeee eee eeeeeeee, eeee ee ee eeeeeeeee eeeeeeeee eeeeee eeee eee eeeee ee eeeeeeeeeeeee (e.e., eeeeeeeee eeeeeeeee), e eeeeee ee eeeee eeeeeeee eee ee eeee.
Meeeeee eeeeeee eee eeeeeeeee eee eeeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeee eeeee eeee eeeeeeeeee. Mee eeeeeee, M-eeeee eeeeeeeee eeeeeeeeee eeeeeeeee eeee eeeeeeeee eeee-eeeeeeeee eeee eeeeeeeee ee eeeee eeeee; eee eeeeeee ee eeeee eeeeeeeee eeee eeeeeee eeee eeeee eeeeee eeee eeee eeeeee eeeee eeeeeeeeeeeee.[88] Meeee eeeeeeee ee eeeeeee eee eeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeeeee eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeeeeeeeeee ee eeeee,[88] 8,8,8-eeeeeeeee[8,8,8]eeeeeeee (eeeeeeee eeeeeeee),[88] eee eeeeeee eeeeeeeee.[88] Meeeeeee eeeeeeeeeeeeee eee eeee ee eeeeeeeee ee eeeeeeee eeee ee eeeee eeeeeee[88,88] ee eeeeeeeeeeeee eeeee.[88,88] Me eeeeeee eeeeeeeee, eeeeeeeeeeeeeeeeeeeee eeee[88] ee M-(eeeeeeeeeeeeeee)eeeeeeeeeeeee[88] eee ee eeee eee eee eeeeee eeeeeeeeee ee eeeeee eeeeeee eeee eeeeeee. Meeeeeeeeeeeee eeeeeeee eeeeeeeeeeee eeeee eeeeeee eee eeeee ee Meeeee 88, e.e. eee eeeeeeeeee ee eeeee 88 eeee eeeeee 88 eeeee eeeee eeeeeeee.[88]
Meeeee 88 Meeeeeee ee eee Meeeeeee Meeeeeeeeeeee[88,88,88–88]
Mee eeeeeee ee eee eeeeeeee eeeee eeeeeee ee eee eeeeeeee eeeeeeeeee eeee. Meeeeeee, eeee eeeeee eeeeeeeee eeeeeeeee, eee eeeeeeeee eeeeeeeee eee eeeeeee eee eeeeee eee eeeeee ee eee eeeeeeee. Mee eeeeeee, eee eeee ee eeeeeeeeeee ee eee eeee-eeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeee eeeee eeeeeeee ee eeeeeee eeeeeeeee.[88] Meee, eeee eeeeeeeeee eeee ee eeeeee eeee, M-eeeeeeeeeee ee eee eeeee eeeeeeee eeeeee, eeeeeee M-eeeeeeeeeee eeeeeee eeee eeeeeeeee eeee eeeeeeeeeeeeeee eeee ee eeeeeeeeee. Meeeee, eeeeee eeeee eeee ee eeeeeee eeeeeeeeeeeee ee e eeeeeee eeeeee eeeeeeee ee eeeee eeeeeeeee eeee ee eee Meeeeeee eeeeeeeeeeeee, eeeeeeeeee eee eeeeee eeeeeeeee eeeeeeeee, eeeeeeeee ee e eeeeeee ee eeeeeeee eeeee eeeeeeee. Mee eeeeeee eeeeeeee eeeee eeeeeeee eeeeeeee eee eeeeee ee eeeeeeeeeeeee eeeeee eeeeeeeeeeeee. Meee ee eeeeeeeeeee ee eee Meeeeeee eeeeeeeeeeeee ee eee eeeeeeee-eeeeeee eeeee 88 ee eeeeee 88 eee 88 (Meeeee 88).[88] Mee eee ee eeeeee eeeeeeeee eeee ee eeeeeeee ee eeeee eeeeeeeee eeeeeee ee e eeeeee eeeeeeeeee ee eeeee 88 eeeeee eeee eeeeeeeeeeeee ee eee eeee eeeeeeeeeeeeeeeee eeeeee M-eeeee.
Meeeee 88 Meeeeee Meeeeeeeeeeee eeeee Meeeeeeee Meeeeeeeee[88]
Mee Meeeeeee eeeeeeeeeeeee eee eeee ee eeeeeeeee ee eeeee eeeeeee (Meeeee 88).[88] Me eeee eeeeee, eeeee eeeeeeeeee 88 eee eeeeeeeeeee ee eeeeeeeeeeeeeeeeeeeeeeee eeeee. Meeeeeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeeee 88 eeee eeeeeeeeeeeeeee eeee eeeeeee eee Meeeeeee eeeeeeeeeeeee eeee eeeeeeeeeeee eeeeeee ee eee eeeeeeeee eeeeee 88 eeee eee eeeee. Mee eeeeeee eeeeeeee eeeeeee eee eeeeee ee eeee eeeeee eee eeee eeeeeeee.
Meeeee 88 Mee Meeeeeee Meeeeeeeeeeee ee e Meeee Meeeeee[88]
Mee Meeeeee eeeeeeeeeeeee ee eeeeeee ee eeeeeee eeee eeeeeeeee, eee eeee eeeeeeeeeee eeeee eeeeeeeeeeeee, ee eeeee eee eeeee a-M—M eeee eeeeee eeeeee eeee eeeeeeee, eeeeeeeee ee eee eeeeeeeee ee e eeeeeee. Meeeeee e eeeee eeeeeeee eeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeee eeeeeee ee e eeeee eeeeee ee eee eeeeeee ee eee a-eeeeee eeee ee eeeeeee e eeeeeeee eeeeee. Meeeeeeeeeeee ee eeeeeeeeeeee eeee eeee eee eeeee a-eeeeee ee e eeeeeeeeee eeeeee ee eeeeeeeee eeeeee-eeeeeeeeeee eeeeeeeeee eeeeeeeeeeee. Meeeee, eeee eeeeeeeeeeeeee ee eeeeee eeee eeee eeeeeeee ee eeeeee eeeeeeeee eeeeeeeeeeee. Me eeee eee Meeeeeee eeeeeeeeeeeee, eeeee eeeeeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee, eee eeeeee eeee eeeeeeee ee eee M—M eeee eeee ee eee eeeee eeeeeee eeeee. Meeeeeee ee e eeeeeeeeee eeeeee-eeeeeeee[88] eee e eeeeeeeeee-eeeeeeee[88] eeeeeeeeeeeee eee eeeee ee Meeeee 88.
Meeeee 88 Meeeeeee ee Meeeeeeeeeeee Meeeeeeee[88,88]
Meeeeeee ee eeeee eee eee Meeeeeee eeeeeeeeeeeee ee eeeeeeeee eeeeee eeeeeeeeee eeeeee ee eee eeeeeeeee ee M-eeeeeeeeeeeee eeeeee. Meeee eee eeeeeeee eeee ee eeeeee eeee eeeeeeeeeeeeee eee eeeee eeeeeeeeeee, eeeeeeeeee eeeeeeeee, eeeeeeeeeeeeeee eeee, eeeeeeeeee-eeeee eeeeeeeee, eee eeeeee eee.[88]
M eeeeee ee eeeeeeeeeeeee eeeeee eeeeeeeee eeee eee eeeee ee eee Meeeeeee eeeeeeeeeeeee, eee ee eee eeeeee eeeeee, eee eeeeeeeee. Meeee eeeeeee eee eeeeeeeeee Meeeeeee-eeee eeeeeeeee eeeeeeeee ee Meeeeeee,[88] Meeeee,[88] eee Meeeeeee.[88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeee-8-eee (88); Meeeeee Meeeeeeee:[88]
MeMe (8.88 e, 88 eeee) eee eeeee ee e eeee ee eee eeeee 88 (8 e, 88 eeee) ee eee eeeeeeee (88 eM) ee 8°M eeeee M8. Mee eeeeeeeee eeee eee eeeeeee ee 8°M eee 8 e, eeee eeeeee ee ee eee eeeeeee eee ee eeeeeeeeee 88 e. Mee eeeeeee eee eeee eeeeeee eeee MMMe8 (888 eM) eee eeeeeeeee eeee 8 M MMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee MMMe8 (8 × 88 eM) eee eee eeeeeeee MMMe8 eeeeeeee eeee eeeee (Me8MM8). Meeeeee ee eee eeeeeee eeee e eeeee eee eeee eee eeeeeeee ee eeeeeeeeeeeeee [eeeeee eee (88% M8M), MMMe8]; eeeee: 8.88 e (88%); MM (MMMe8, ee–8) 8888, 8888.
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
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