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Yliniemelä-Sipari, S. M.; Pihko, P. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 661.
Aliphatic nitro compounds enolize more readily than aliphatic ketones or aldehydes. In water, the pKa of nitromethane is ca. 10, whereas the pKa of acetone is 19.1.[31] In addition, the nitro group cannot act as an electrophile in aldol-type reactions; the enolized nitro compounds always act as nucleophiles and readily add to aldehydes in a process called the nitroaldol reaction. The nitroaldol, or Henry reaction, named after L. Henry who discovered the reaction in 1895,[171] is a particularly attractive method for the stereoselective construction of C—C bonds.[172–175] The product is a β-nitro alcohol (nitroaldol). The nitro alcohol products can be transformed into a number of valuable nitrogen- and oxygen-containing derivatives such as nitroalkanes, amino alcohols, and carboxylic acids.
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References
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[171] | Meeee, M., M. M. Meee. Meeeeee Meee. Mee., (8888) 888, 8888. |
[172] | Mee, M., Mee Meeee Meeee ee Meeeeee Meeeeeeee, Meeee-MMM: Mee Meee, (8888). |
[173] | Meeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee.; Meeeeeee: Mee Meee, (8888); Mee. 8, e 888. |
[174] | Meeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
[175] | Meeeee, M.; Meeeeeee, M.; Meee, M., Mee. M. Mee. Meee., (8888), 8888. |
[176] | Mee, M.; Meee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[177] | Meeeeeee, M.; Meeeeee, M. M.; Møeeeeeee, M. M., Mee. Meeeee. Meee., (8888) 8, 888. |