1、- Aromatic Reactions - Condensation - Cyclization - Epoxide Transformation - Olefination - Oxidation - Reduction - Rearrangement Condensation Olefination Oxidation Rearrangement Reduction Cyclization Aromatic Reactions topCommon Transformation of Epoxide top“.a recent memoir by a Herr vant Hoff on “
2、the Arrangements of Atoms in Space,“ a document crammed to the hilt with the outpourings of a childish fantasy.This Dr. J.H. vant Hoff.no taste for accurate chemical research.“ By H. Kolbe (one of the most eminent organic chemist of the time). 10 years later vant Hoff was named the first recipient o
3、f the Nobel Prize in Chemistry.AAcetoacetic Ester Synthesis is a very useful basic reaction in ether industry or academia. The methylene group in acetoactic ester could be easily alkylated, and double alkylated under basic condition. One condition I used frequently is acetone as solvent, K2CO3 as ba
4、se, and alkyl bromide as alkylation reagent. The reaction rarely lets me down. Simonsen, J.L.; Storey, R. J. Chem. Soc. 1910, 95, 2106Simonsen, J.L.; Storey, R. Proc. Chem. Soc. 1910, 25, 290 Click here to learn more. Alder (Ene) Reaction is thermal or catalytic sigmatropic rearrangement with H-tras
5、fer and carbon bond formation. Click here to learn more.Aldol condensation is a reaction that generated lots of Ph.D. in organic synthesis. No need to talk about it. The aldol condensation using aldehyde and silyl enol ether as starting materials, and lewis acid, like TiCl4, as catalyst is called Mu
6、kaiyama aldol condensation. Kane, R. Ann. Phys. Chem. Ser. 2 1838, 44, 475Kane, R. J. Prakt. Chem. 1838, 15, 129 Click here to learn more.Algar-Flynn-Oyamada Reaction is the synthesis of flavonols via the intermediate dihydroflavonols made by oxidation of o-hydroxyphenyl styryl ketone using hydrogen
7、 peroxide. Click here to learn more.Allen-Millar-Trippet rearrangement. Click here to learn more.Amadori Rearrangement is the conversion of N-glycosides of aldoses to N- glycosides of the corresponding ketones. Click here to learn more.Angeli-Rimini hydroxamic acid synthesis Click here to learn more
8、.Appel Halogenation Click here to learn more.Arndt (Fritz Arndt 1885-1969) -Eistert (Bernd Eistert 1902-1978) rearrangement is used in the conversion of a carboxylic acid into its homolog or derivatives of the homologous acid. If the reaction intermediate could be quenched to give alpha-halo ketone.
9、 Click here to learn more.Asinger Thiazoline Synthesis Click here to learn more.Auwers reaction is the expansion of coumarones to flavonols. K. v. Auwers et al., Ber. 41, 4233 (1908); 48, 85 (1915); 49, 809 (1916)K. v. Auwers and P. Pohl, Ann 405, 243 (1914)Click here to learn more.Azo coupling Clic
10、k here to learn more.B C topBaeyer Pyridine Synthesis Click here to learn more.Baeyer (Johann Friedrich Wilhelm Adolf von Baeyer 1835 - 1917) -Villiger (Victor Villiger 1868 - 1934) Oxidation is an oxidative rearrangement reaction initiated by nucleophilic attack. The order of migratory aptitude is
11、3o-alkyl 2o-alkyl benzyl phenyl 1o-alkyl cyclopropyl MeH. If it is used in phenyl aldehyde to make phenol, the reaction is called Dakin oxidation. Click here to learn more. Johann Friedrich Wilhelm Adolf von Baeyer, Nobel Prize Chemistry 1905.Baker (Wilson Baker b.1900) -Venkataraman rearrangement i
12、s the rearrangement of o-keto ester of phenol to o-hydroxy-1,3-diketone. The 1,3-diketone could cyclize to form flavone. Click here to learn more.Bamberger (Eugen Bamberger 1857-1932) rearrangement is the intermolecular rearrangement of N-phenylhydroxlamines to the corresponding 4-aminophenol under
13、acidic condition. Click here to learn more.Bamberger imidazole cleavage Click here to learn more.Bamford (W. R. Bamford) -Stevens-Shapiro Olefination is a base-catalyzed decomposition of arenesulfonylhydrazones of aldehydes and ketones, leading to the formation of alkenes. Click here to learn more.B
14、arbier (Francois Antoine Phillipe Barbier 1848-1922) Reaction is the one-pot procedure for the preparation of alcohols from organic halides and aldehydes or ketones. Click here to learn more.Bargellini reaction is using a ketone and CHCl3 generate a dichloro epoxide, which react with a hydroxyl amin
15、e or diamnio ethane derivative to form highly hindered morpholinone or piperazinone. Click here to learn more.Bartoli (Giuseppe Bartoli) indole synthesis is the synthesis of indoles reductively by o-substituted nitrobenzene and allyl grignard. Click here to learn more.Barton (Derek H. R. Barton1928
16、-1998) deamination Click here to learn more.Barton decarboxylation Click here to learn more.Barton deoxygenation is the deoxygenation of alcohols via their thiocarbonyl derivatives. Click here to learn more.Baylis (A.B. Baylis) - Hillman (M.E.D. Hillman) Reaction is the activated vinyl system to rea
17、ct with ketone or aldehyde to yield alpha-hydroxyl products. Click here to learn more.Beckmann (Ernst Otto Beckmann 1853 -1923) Rearrangement is acid (P2O5, PCl5, H2SO4 etc) catalyzed rearrangement of oxime to amide or nitrile. Click here to learn more.Benzilic acid rearrangement is base-induced rea
18、rrangement of benzil to benzylic acid via phenyl group migration. Liebig, J. Ann. Chem. 1838, 25, 27Zinin, N. Ann. Chem. 1839, 31, 329 Click here to learn more.Benzoin Condensation is cyanide-catalyzed condensation of aromatic aldehydes to give benzoins. Lapworth, A.J. J. Chem. Soc. 1903, 83, 995Lap
19、worth, A.J. J. Chem. Soc. 1904, 85, 1206 Click here to learn more.Bergman (Robert George Bergman) Cyclization is the cyclization of enediynes to generate 1,4-benzenoid diradicals. Click here to learn more.Bernthsen Acridine Synthesis is the synthesis of 5-substituted acridines by diarylamines in org
20、anic acids or anhydrides. Click here to learn more.Biginelli pyrimidone synthesis is the 3 components formation of tetrahydropyrimidinones. Click here to learn more.Bischler - Mohlau indole synthesis is the formation of 2-substituted indoles by heating alpah-halo or hydroxy-ketone with excess amount
21、 of aniline. The excess amount aniline is highly important for the success of reaction and mechanism. This is a proposed mechanism from a experienced colleague. Click here to learn more.Bischler (August Bischler 1865 - ?) - Napieralski (Bernard Napieralski ) Isoquinoline synthesis. Bischler - Napier
22、alski reaction is similar to Morgan -Walls reaction (Pictet - Hubert reaction). Click here to learn more.Blanc-Quellet chloroalkylation Click here to learn more.Blicke-Pachter Pteridines synthesis Click here to learn more.Blum Aziridine synthesis Click here to learn more.Boekelheide reaction Click h
23、ere to learn more.Boger pyridine synthesis is a hetero Diels-Alder reaction. Click here to learn more.Bouveault aldehyde synthesis Click here to learn more.Brandi-Guarna rearrangement Click here to learn more.von Braun reaction is the degradation of a tertiary amine with cyanogen bromide or chlorofo
24、rmate. Click here to learn more.Brook (Adrian Gibbs Brook 1924 - ) Rearrangement Click here to learn more.Brown hydroboration not only could make hydroxyl group but also could make amino group. Brown, H.C.; Subba Rao, B.C. J. Am. Chem. Soc. 1956, 78, 5694Brown, H.C.; Subba Rao, B.C. J. Org. Chem. 19
25、57, 22, 1135; 1136 J. Org. Chem. 1981, 46, 4296; J. Am. Chem. Soc. 1964, 86, 3565. Click here to learn more.Bruylants amination Click here to learn more.Bucherer (Hans Theodor Bucherer 1869-1949) - Bergs Hydantoin synthesis Click here to learn more.Buchner-Curtius homologation Click here to learn mo
26、re.Burgess dehydrating reagent Click here to learn more.C B topCannizzaro (Stanislao Cannizzaro 1826 - 1910) disproportination reaction tells that aldehyde is not very stable under basic condition. Click here to learn more.Carroll rearrangement Click here to learn more.Chapman (Arthur William Chapma
27、n 1898 - ?) rearrangement Click here to learn more.Chichibabin (Alexei Yevgenievich Chichibabin 1871 -1945) pyridine synthesis Click here to learn more.Chugaev (Lev Aleksandrovich Chugaev 1873 - 1922) elimination is the hydroxyl group reacts with CS2, followed by methylation to form xanthate. The sm
28、ell of this reaction is not very good, because it will release methyl thiol. Click here to learn more.Ciamician-Dennstedt cyclopropanation. Ciamician-Dennstedt rearrangement is the rearrangement of cyclopropane formed from dichlorocarbene. Click here to learn more.Claisen-Geuter-Dieckmann ester cond
29、ensation Click here to learn more.Claisen (Rainer Ludwig Claisen 1851-1930) - Ireland Rearrangement is a 3,3 sigmatropic shift. Click here to learn more.Clarke (Hans Thacher Clarke 1887 - 1927) - Eschweiler reductive amination is especially for the methylation of amino group, another reductive amina
30、tion reaction with similar mechanism iscalled Leuckart-Wallach reaction that ketone or high level aldehyde is used instead of fomaldehyde. NaBH3CN is also used in reductive amination under mild acidic condition. Click here to learn more.Clauson-Kaas Pyrrole synthesis Click here to learn more.Combes
31、quinoline synthesis Click here to learn more.Comins reaction Click here to learn more.Conrad-Limpach reaction Click here to learn more.Cook-Heilbron thiazole synthesis Click here to learn more.Cope elimination reaction is the syn-elimination of N-oxides of tertiary amines. You can compare this react
32、ion with another elimination, Hofmann elimination, in which a quaternary ammonium slat undergoes elimination to form less substituted olefin. The leaving hydrogen is more acidic or less hindered. Hofmann elimination was used a lot in early stage alkaloid structure identification. Click here to learn
33、 more.Cope (Arthur Clay Cope 1909 - 1966) Rearrangement is the conversion of a 1,5-hexadiene derivative by the 3,3-sigmatropic mechanism. The reaction is both stereospecific and stereoselective. Click here to learn more.Corey (Elias James Corey 1928 - ) - Bakshi - Shibata Reduction, oxazaborolidine
34、(CBS reagent), is used to reduce a ketone enantioselectively by borane. The catalyst can be made from L-proline or D-proline. You can buy commercially available catalysts from Aldrich. The enantioselectivity is obtained by the different steric hinderance between large and small groups in ketone. Corey, Nobel Prize Chemistry 1990. Click here to learn more.Corey-Chaykovsky sulfur ylide reaction Click here to learn more.Corey - Kim (A.U. Kim) Oxidation
