You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.21.1.5.8 Method 8: Willgerodt Reaction from Aryl Ketones
Please login or sign up for a free trial to access the full content.
Judd, W. R.; Katz, C. E.; Aubé, J., Science of Synthesis, (2005) 21, 173.
The Willgerodt reaction involves the conversion of an aryl alkyl ketone, e.g. 119, into an amide, e.g. 120, containing the same number of carbons by heating with aqueous ammonium polysulfide. The terminal methyl group of the ketone alkyl substituent is always converted into the carbonyl moiety of the resulting amide regardless of its position relative to the original carbonyl group. Thus, the overall transformation results in the formal reduction of the original carbonyl group to a methylene, and the oxidation of the terminal alkyl carbon to afford an w-alkylaryl amide (Scheme 55).[130,133] The Willgerodt reaction therefore has some formal similarity to the Arndt–Eistert synthesis (see Section 21.1.5.2).
Meeeee 88 Mee Meeeeeeeee Meeeeeee[888,888]
Meeeeee eeeeeeee eeeeeeeeeeeeee, eee eeeeeeeeeee eeeeeee ee eee eeeeeeee eeee eee eeee eeeee eeeeeeeeee. Meeee eee eeeeee ee eeeeeeeee eeeee ee eeeeeeee eeeeeeeee eeee eee ee eeee, e eeeeee eeeeeeeee eee eee ee eeeeeeeeee ee eeeee eeeeeee ee eee Meeeeeeeee eeeeeeee. Meeeeee eeeeeee eeeeeeeeee eee eeeeee ee eee eeeeeeeeeeeeee eee, eeeeeee, eeeee. Me eee eeee eeeeeeeeeeee eeeeeeeeeee eeee eeeeeeee eeeeeeeeeeeee eeee eee eeeee.[888] Meeeeeee, ee eeeeeeeeeeeee eeeeee (e.e., eeeee eee ee eeeeeee ee eee eeeeee eeeeeeee) eeeeee eee eeeeeeeeee ee eee eeeeee eeee eee eeeee eeeeeee. Me ee eeee eeeeeeeeeee ee eeee eeee eeeeeee eeee eeeeee eeee ee eee eeeeeeee ee eee eeeeeeee eeeee eeee eeeeeeeee eeeeeeee.
Meeeeeee eeeeeeeeeeeee ee eee Meeeeeeeee eeeeeeee eeee eeee eeeeeeeeee. Mee eeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeee ee e eeeeee eeee ee eeee eeeeeeeeeeee (~888–888°M) ee eeeeeeeeeeee eeeeeeee ee eee eee ee eeeeeeee eeeeeee, eeeee eeeeeee eee eeeeeeee ee eeee eeeee ee 888°M.[888] Meeeeeee ee eeee eeeeeeeeee eeee ee eee eeeeeee. M eeeeeeeeeee ee eeeeee eee eeeeeeee eeeeeeeee eee ee eeee ee e eeeeeeeeee eee eeeeeee eeeeeeee eeeeeeeeeee, eeeeee eeeee ee ee eee eeeeeeee ee eeeeeee ee eeeeeeee.[888] Me eeeeeee, eeeeeeeeee ee eeeee e eeeeeee ee eeee eeee eeeeee eeeeee, eeeeeeee ee e eeeeee ee eee eeeeeeeee eeeeeeeeee ee eee eeeeee eee eeeeeee eeeeeeeeeee.[888] Mee Meeeeeeeee eeeeeeee eee eeee ee eeeeeee eee ee e eeeeeeeee eeeeeee, eeeeee eeeeeeeeeeee eeeeee ee eee eeeee eeeeeee eeee eeeeeeeeeeee eeeeeeeee eeeeeeee eeeee.[888]
Mee Meeeeeeeee eeeeeeee eee ee eeeeeee ee e eeee eeeee ee eeeeeeeeeee eeeee eeee eeeeeee, eeeeeeeeee eeeeee eeeeeeee- ee eeeeeeee-eeeee eeeee eeeeeeeeeeee; eeeeeee, eee eeeeee eeeeeeee eeeeeee eeee eeeeeeeeee eeeeee ee eee eeeee eeeee. Mee eeeeeeee ee eeee eeeeeeeeee ee eeeeeee eeeeeee, eeeeeeee eee eeeeee eeee eeeee eeeeeeeeee eee eeeeeeeee eeeee. Me eeeeeee eeeeeeeeee eee eeeeeeeee eeeee eeeeeeeeeeee, eee eeeeeeee eeeeeeeee ee eee eeeeeeee eeeee eeeeee eeeeeeeeeeeeee eeeee eee eeeeeee eee eeee-eeeeeeee eeeee eeeee.[888] Meeeeeee eeeeeeeee eeee eeeee eeeeeeeeeeee eeee eeee eeee eeeeeee ee eeeeeee ee eee eeeeeeee; eeeee eeeeeeeee eeeeeee e eeeeeeee eeeeeeee, eeeeeeeee eeeeeee, eeeeeeeeee, eeeeeeee, eee eeeeee, eee eeee ee eeeeeeeee eeee eee eeeeeeeeeeeee eeeee eeeeeee ee eeee eeeeee.[888] Mee eeee eeeeeeeee eeeeeeeeeee ee eee Meeeeeeeee eeeeeeee eeeeeee, eeeeeee, eee eeeeeeeee ee eeee eeeee eeeeee eeee eeee eeeee eeeeeee.
Meee eeeeeeeee eee eeeeeeee eeee eee eeeeeeee eeeeeeee eeeeeeee eeeeeeee eeeeeeeeee eeeeee, eeee ee eeeee, eeeee, ee eeeeee, eeee eee eeeeeeeeeee ee eeeeeeeee, eeeeeeeee, ee eeeeeeeeeeee eeeee eeeeeeeeee ee eee Meeeeeeeee eeeeeeee. Me eeeeeeee, eeeeeee eeeeeeeeee eee eeeeeeeee eee eeeeeee eeeee eeeeeeeee ee eee eeeeeeee. Mee eeee eeeeee ee eeeee ee eee eeeeeeee eeee ee eee eeeeeeeeeeeee eeeeeeeeee eeee. Mee eeeeeeeeeeeee eeeeeeeeeeee eee eeee eeeeeeee eeeeeeee, eeeeeeee ee e eeeeee ee e eeee eeeeeeeeeeeee ee eeeeeeee eeeeeee (eeeeeeee ee eee eeeeeeeeee ee eeeeeeee eeeeeeeeeee eee eeeeeeee eeeeee eee eeeeee ee eee eeeeeeee). Meeee eeeeeee ee eeeeeeeeee eee eeeeeeee eeee eeeeee eeee eeeeeee. Mee eeeeeeeeee ee eeee eeee ee eeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeee eeeeeee ee eeee ee eeeee ee eeeeeeee eeeeeeeeeee.[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeee eeeeeeee eeeeeeee ee e eeeeee eeeeee eeeeeeee eeeeee eeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeee eeeeeeeee. Mee ee e eeeee eeeeee ee eeee eeeeee eeeeeeeeeee. Meeeee ee e eeeeeeeee eeeeeeeee eeeeee.
Meeeee M: MeMMMe (888; 88.8 e, 888 eeee), M8 (88.8 e), 88 M eeeee ee MM8MM (88 eM), eee eeeeeeee (88 eM) eeee eeeeee ee e 88-ee eeeeeee eeeeeeee eeee-eeeee (eee Meeee) eeee eeee eee eeeeee ee 888°M eee 8.8 e. Mee eeee eee eeeeeee ee eeee ee ee, eee eeee eeeeee. Mee eeeeeee eee eeeeeeeeeeee ee eeeeeee. Mee eee eeeeeee ee eeeeee eee eeeeeee eee eeeeeeeee eeee eeeeeee M8M (ee. 888 eM) ee eeeeeee eeeeeeee. Mee eee eeeee eeee eeeeeeeee eeee eeeeeeee eee eeeeeeee. Me eeeeeee eee eeeeeeee, 8-eeeeeeeeeeeeeee (88.8 e) eeeeeeeee eeee eee eeee. Meeeeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeeee 8-eeeeeeeeeeeeeee (8.8 e); eeeee eeeee: 88.8 e; ee 888–888°M.
8-Meeeeeeeeeeeeee (888) ee Meeeeeeee Meeeeee; Meeeeee Meeeeeeee:[888]
Meeeee M: M eeeeeee ee M8 (88.8 e, 88.8 eeee), eeeeeeee (88 eM), 88% ee MM8 (88 eM), eee MeMMMe (888; 88.8 e, 88.8 eeee) eee eeeeee ee 888°M (eeeeeee eeeeeeee 8.88 MMe) eee 88 eee eeee eeeeeeee ee e eeeeeeeee eeeeeee. Mee eeeeeee eee eeee eeeeeee eeeeee eee eeee eeeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeeee ee Me8M (88 eM) eee eeeeeeee. Mee eeeee eee eeeeee eeee Me8M (8 × 88 eM), eeeeeeeee ee eeeeeee M8M (~8 M), eee eeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeeeeeee eeee MM8Me8 (888 eM) eee 88 e eee eee eeeeeee eeeee eee eeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeeeeeeeee (MM8Me8) ee eeeeeeeee eeeeee; eeeee: 8.8 e (88%).
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
eng_Latn eng_Latn eng_Latn knc_Latn eng_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn bam_Latn lit_Latn bam_Latn por_Latn lvs_Latn bam_Latn kam_Latn kam_Latn ibo_Latn ibo_Latn