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"...a recent memoir by a Herr van't Hoff on "the Arrangements of Atoms in Space," a document crammed to the hilt with the outpourings of a childish fantasy...This Dr. J.H. van't Hoff...no taste for accurate chemical research..." By H. Kolbe (one of the most eminent organic chemist of the time). 10 years later van't Hoff was named the first recipient of the Nobel Prize in Chemistry.
A
| Acetoacetic 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 base, and alkyl
bromide as alkylation reagent. The reaction rarely lets me down.
Simonsen, J.L.; Storey, R. J. Chem. Soc. 1910, 95, 2106 |
|
Alder (Ene)
Reaction is thermal or
catalytic sigmatropic rearrangement with H-trasfer 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 Mukaiyama aldol condensation.
Kane, R. Ann. Phys. Chem. Ser. 2 1838, 44, 475 |
| Algar-Flynn-Oyamada Reaction is the
synthesis of flavonols via the intermediate dihydroflavonols made by
oxidation of o-hydroxyphenyl styryl ketone using hydrogen 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. |
| 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. 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) |
| Azo coupling Click here to learn more. |
| Baeyer 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 3o-alkyl
> 2o-alkyl > benzyl > phenyl > 1o-alkyl >
cyclopropyl >Me>>H. 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 is 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 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. |
| Barbier (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 amine 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 -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 react 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 rearrangement of benzil to benzylic acid via phenyl group
migration.
Liebig, J. Ann. Chem. 1838, 25, 27 |
| Benzoin Condensation is
cyanide-catalyzed condensation of aromatic aldehydes to give benzoins.
Lapworth, A.J. J. Chem. Soc. 1903, 83, 995 |
| 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 organic 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 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 - Napieralski 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 here 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 chloroformate. 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, 5694 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 more. |
| Burgess dehydrating reagent Click here to learn more. |
| Cannizzaro (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 Chapman 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
smell 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 condensation 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
amination 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
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 reaction 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 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 (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. Click here to learn more. |
|
Corey-Chaykovsky sulfur ylide reaction Click here to learn more. |
| Corey - Kim (A.U. Kim) Oxidation Click here to learn more. |
| Corey-Link reaction Click here to learn more. |
| Corey-Seebach reaction Click here to learn more. |
|
Corey - Winter (Roland Arthur Edwin Winter
1935 - ) olefination is the synthesis of alkenes from vicinal diols.
This method has been particularly useful in synthesizing substrates with
delicate structure features such as strained and twisted olefins,
unsaturated carbohydrates, macrocyclic lactones, as well as in
establishing the stero-chemistry of diol functions in natural products. Click here to learn more. |
| Cornforth (John Warcup Cornforth 1917 - ) oxazole rearrangement Click here to learn more. Cornforth, Nobel Prize Chemistry 1975 |
| Criegee (Rudolf Criegee 1902 - 1975) ozonolysis is a very clean
reaction. Criegee glycol oxidation is the oxidation of 1,2-glycol
to two carbonyl by lead tetraacetate (LTA). Click here to learn more. |
| Curtius (Theodor
Curtius 1857-1928) rearrangement Click here to learn more. |
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Corey,
Nobel Prize Chemistry 1990.
