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Hashmi, A. S. K., Science of Synthesis, (2007) 25, 329.
Commercially available disodium tetracarbonylferrate (44),[120] for which an excellent preparative procedure is available,[121] can be used instead of a carbonylhydridoferrate, but the acyl complex that is formed after alkylation is anionic, and acid treatment is required to liberate the aldehyde 45 (Scheme 12).[122] Triphenylphosphine can also be added to facilitate the workup.[121] Ester groups on the substrate are tolerated.[122] Electrochemical reduction of pentacarbonyliron(0) in acetonitrile, followed by the subsequent addition of an alkyl halide and an acid, also gives the corresponding aldehyde.[123] Detailed studies have been made of both the oxidative addition[124] and the alkyl migration[125,126] steps in the reaction of the ferrates with alkyl halides.
Meeeee 88 Meeeeeeee eeee Meeee Meeeeeee eee Meeeeeeeeeeeeeee[888,888]
M8M | Meee/Meeeeeee | Meeee (%) ee 88 | Mee |
---|---|---|---|
Me(MM8)8Me | MeMM/Me8M | 88 | [888] |
Me(MM8)8Me | MeMM/Me8M | 88 | [888] |
Me(MM8)8Me | MeMM/Me8M | 88 | [888] |
MeMM8Me | MeMM/Me8M | 88 | [888] |
Me8M=MMMM8MM8Me | MeMM/Me8M | 88 | [888] |
Me(MM8)8MM(Me)Me | MeMM/Me8M | 88 | [888] |
MeM8M(MM8)8Me | MeMM | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
Meeeee 8-Meeeeeeeeeeee [88, M8 = (MM8)8MM8Me]; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.
MMMMMMM: Meeeeeeeeeeeeeeee(8) ee e eeeeeeeee eeeeeeee. Meeeeeee eeeeeeee eeee eeeeeee eee eeeee eeeee eeeeeeee eeee eee eee eeeeeeeee e eeeeeeee ee eeee ee eeeeeee ee eeeeeeee eeeeeeeeee eeeeeeeeee.
M eee, 8-M, eeeee-eeeeee, eeeee-eeeeeeee eeeee, eeeeeeee eeee e eeeeeeeeee eeeeeee, e eeeeee eeeeeeeee, eee e eeeee-eee eeeeeeee eeee eee eeeeee eeeeeeeee ee e eeeeee ee M8, eee eeeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeee[888] (88.8 e, 888 eeee) eee eee eeeeeeeeeeee MMM (8.8 M). Mee eeeeeeeeee eee eeeeeee eeeeeeeeee eeeee eeeeee 8-eeeeeeeeeeeeee (88.8 e, 888 eeee) eee eeeee ee eee eeeeeee ee eeeeeee. Mee M8 eee eeeeeee eeee eee eeeee eeee MM eeeeeee eee eeeee eeeeee ee eee eeeee-eee eeeeeeee, eee eee eeeeeeeeee eee eeeeeee eeeee 8.888 MMe ee MM eee ee eeeee 88 e eeeee eee eeeee eeeeeeeee. M eeeee eeee ee M8 eee eeeeee eeeeeee eee eeeee eeeee eee eeeeee eee eeeeeee eee eeeeeeee eeeeeee eeee e eeeeeeee-eeeeeeeeee eeeeeeee eeeeee. Mee eeeeeeee eeeeee eee eeeeeee eeee M8 eee eeeeeee eeee eeeeeee MeMM (88 eM). Mee MeMM eee eeeee eeeeeeee ee eee eeeeee eeee ee eee eeeee, eee eee eeeeeee eee eeeeeee eee 88 eee ee eeee e eeee eee eeee, eeeee eee eeeeeeeeeeee ee eeeee 888 eM ee e eeeeee eeeeeeeeee ee e eeee [MMMMMMM: Meee Me(MM)8 ee eeeeeee]. Mee eeee eee eeeeee eeee M8M (8 M) eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (888 eM) eee eeeee eeee 8 M MMe (888 eM). MeMe8 (88 e) eee eeeee ee eeeee eeeeeeee, eeeee eeeeeeeee ee MM eeeeeeee eee eee eeeeeee eeeee eeeeee eeeee. Mee eeeeeee eeeee eee eeeeee eeeeeeeeeeee eeee 888-eM eeeeeeee ee 8 M MMe, M8M, eee. ee MeMMM8, eee eee. eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee e eeeeee eeeeeeeeee ee eeee e eeeee eee. Meee-eeeeeeeeee eeeeeeeeee eeee eeeeeee ee eeeee eeeeeeeeeeeeee [8 × 88 ee eeeeee, eeeeee (8 M) eeee Me8M/eeeeee 8:8 (8 M)]. Mee Me8M/eeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee ee eee eeee eee eeeeeeeee eeeeeee e 88-ee Meeeeee eeeeee ee eeeeeee eeeeeeee; eeeee: 88.8 e (88%); ee 88–88°M/8.8 Meee.
References
[120] | Meeeeee, M. M., Mee. Meee. Mee., (8888) 8, 888. |
[121] | Meeee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[122] | Meeee, M. M., Me., M. Me. Meee. Mee., (8888) 88, 8888. |
[123] | Meeeeee, M.; Meeeeeee, M.-e.; Meeeeeeee, M.; Meeee, M.-e., Meeeeeeeeee Meee., (8888) 88, 8888. |
[124] | Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[125] | Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[126] | Meeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.