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Please login to access the full content or check if you have access via8.2.12.2 Method 2: Alkylation and Acylation of Methyl (Methylsulfanyl)methyl Sulfoxide and Thioacetals
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DOI:
10.1055/sos-SD-008-01034
Łaźny, R., Science of Synthesis, (2006) 8, 1233.
The carbanions of this subclass are highly reactive nucleophiles, which can react with a wide range of electrophilic reagents. The alkylation and acylation of sodium derivatives of thioacetals and methyl (methylsulfanyl)methyl sulfoxide followed by hydrolysis provide an umpolung route to ketones and aldehydes.[13,14] Reductive desulfurization with Raney nickel or nickel(II) chloride–sodium borohydride results in functional group removal.[14] The whole sequence of reactions parallels the analogous, highly developed methodology based on lithiation.[15]
References
| [13] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [14] | Meeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [15] | Mee, M.; Máeeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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