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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/18 04:19:35」(JST)
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Chemical reactions are defined usually in small contexts (only up to a small number of neighbouring atoms), such generalizations are a matter of utility. The preferential outcome of one instance of a generalized reaction over a set of other plausible reactions, is defined as chemoselectivity. [1]
In another definition, chemoselectivity refers to the selective reactivity of one functional group in the presence of others; often this process in convoluted and protecting groups are on the molecular connectivity alone.[clarification needed] Such predictions based on connectivity are generally considered plausible, but the physical outcome of the actual reaction is ultimately dependent on a number of factors that are practically impossible to predict to any useful accuracy (solvent, atomic orbitals, etc.).
As such, chemoselectivity can be difficult to predict, but observing selective outcomes in cases where many reactions are plausible, is common. Examples include the selective organic reduction of the greater relative chemoselectivity of sodium borohydride reduction vs. lithium aluminium hydride reduction. In another example, the compound 4-methoxyacetophenone is oxidized by bleach at the ketone group at high pH (forming the carboxylic acid) and oxidized by EAS (to the aryl chloride) at low pH [2]
See also
- Regioselectivity
- Stereoselectivity
References
- ^ IUPAC Gold Book definition for chemoselectivity.
- ^ Ballard, C. E. (2010). "pH-Controlled Oxidation of an Aromatic Ketone: Structural Elucidation of the Products of Two Green Chemical Reactions". Journal of Chemical Education. 87 (2): 190–193. Bibcode:2010JChEd..87..190B. doi:10.1021/ed800054s.
English Journal
- Injectable hyaluronic acid hydrogel for 19F magnetic resonance imaging.
- Yang X1, Sun Y2, Kootala S1, Hilborn J1, Heerschap A3, Ossipov D4.
- Carbohydrate polymers.Carbohydr Polym.2014 Sep 22;110:95-9. doi: 10.1016/j.carbpol.2014.03.070. Epub 2014 Apr 2.
- We report on a 19F labeled injectable hyaluronic acid (HA) hydrogel that can be monitored by both 1H and 19F MR imaging. The HA based hydrogel formed via carbazone reaction can be obtained within a minute by simple mixing of HA-carbazate and HA-aldehyde derivatized polymers. 19F contrast agent was l
- PMID 24906733
- Tertiary amide-based Knoevenagel-type reactions: a direct, general, and chemoselective approach to enaminones.
- Huang PQ1, Ou W, Xiao KJ, Wang AE.
- Chemical communications (Cambridge, England).Chem Commun (Camb).2014 Aug 14;50(63):8761-3. doi: 10.1039/c4cc03826f. Epub 2014 Jun 26.
- We report one-pot and chemoselective Knoevenagel-type reactions using highly stable amides and lactams as the electrophilic substrates. The method is based on the in situ activation of amide carbonyl with triflic anhydride and a subsequent reaction with carbanions generated in situ from carbonyl com
- PMID 24967872
- One-pot, two-step desymmetrization of symmetrical benzils catalyzed by the methylsulfinyl (dimsyl) anion.
- Ragno D1, Bortolini O, Giovannini PP, Massi A, Pacifico S, Zaghi A.
- Organic & biomolecular chemistry.Org Biomol Chem.2014 Aug 14;12(30):5733-44. doi: 10.1039/c4ob00759j. Epub 2014 Jun 26.
- An operationally simple one-pot, two-step procedure for the desymmetrization of benzils is herein described. This consists in the chemoselective cross-benzoin reaction of symmetrical benzils with aromatic aldehydes catalyzed by the methyl sulfinyl (dimsyl) anion, followed by microwave-assisted oxida
- PMID 24967946
Japanese Journal
- Chemoselective and Kilogram-Scale Synthesis of Acetanilide β₃-Adrenergic Receptor Agonist
- Kawazoe Souichirou,Suzuki Takayuki,Nakamura Hirofumi [他]
- Bulletin of the Chemical Society of Japan 88(1), 139-145, 2015-01
- NAID 40020321848
- Nitrogen and oxygen-doped metal-free carbon catalysts for chemoselective transfer hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene with hydrazine
- Fujita Shin-ichiro,Watanabe Hiroyuki,Katagiri Ayaka,Yoshida Hiroshi,Arai Masahiko
- Journal of Molecular Catalysis A: Chemical 393, 257-262, 2014-11-01
- An activatedcarbon(AC)wastreatedbyhydrogenperoxideandammoniatodopeoxygenandnitrogenonits surface.Thesurface-functionalizedACcatalystswereusedforthetransferreductionofnitrobenzene,styrene, and3-nitrost …
- NAID 120005469238
- Nanostructured RuO2 on MWCNTs: Efficient catalyst for transfer hydrogenation of carbonyl compounds and aerial oxidation of alcohols
- Gopiraman M,Babu S. Ganesh,Karvembu R,Kim I.S.
- Applied Catalysis A 484(22), 84-96, 2014-08
- … The RuO2/MWCNT is highly chemoselective, heterogeneous in nature, reusable and highly stable. …
- NAID 120005464848
Related Links
- Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups. A reagent has a high chemoselectivity if reaction occurs with only a limited number of different functional groups.
- Organic Chemistry Terminology for Undergraduate Chemistry Students ... If an organic compound contains more than one different functional groups or more than one like functional groups that are not equivalent (see equivalent ligands ...
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