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S

 Sakurai (Hideki Sakurai 1931 - ) -Hosomi (A. Hosomi) allylation

 Sandmeyer (Traugott Sandmeyer 1854-1922) isatin synthesis

 Scheiner aziridie synthesis

 

 Schmidt  rearrangement is similar to  Curtius rearrangement if the reaction is with the acid. Hydrazoic acid is used in the conversion of carbxylic acid to amide, with aldehyde into nitrile, and ketone into tetrazole or amide.

 

 Schollkopf amino acid synthesis

 

 Schopf reaction

 

 Seyerth acyllithium reaction

 

 Shapiro (Robert Howard Shapiro 1935 - ) reactionis the conversion of ketone p-toluenesulfonylhydrazones to alkenes on the treatment with 2 equiv. of strong bases such as LDA or BuLi.

 

 Sheradsky-Coates-Endo rearrangement

 

Shi asymmetric epoxidation

J. Org. Chem. 2005, 70, 2904-2911    Click here to learn more

 Simchen azaheterocycle synthesis

 

 Simonis chromone cyclization is another phenol and beta-keto ester cyclization.

 

 Skraup (Zdenko Hans Skraup 1850 - 1910) quinoline synthesis

 

Smiles (Samuel Smiles 1877 - 1953) rearrangement is a rearrangement happened on aromatic ring with strong electron-withdrawing group. The result of this reaction is on hetero atom replace another.

 Snieckus rearrangement

 

Sommelet (Marcel Sommelet 1877 - 1952) reaction is the synthesis of aldehyde from primary alkyl halide with hexamethylene tetramine. The second step of this reaction is under basic condition. If the second step is done under acidic condition, the reaction will give primary amine, it is called Delepine reaction.

 

 Sommelet - Hauser (Charles Roy Hauser 1900 - 1970) rearrangement

 

 Speckamp ring closure

 

Staudinger (Hermann Staudinger 1881 - 1965 Nobel Prize Chemistry 1953 ) Azide reduction is a very useful way to make primary amine from azide. A very important transformation in Med. Chem. Another mechanism is the formation of 4-membered ring, and then it decomposes.

 

Stetter (Hermann Stetter 1917 - ) reaction is the Michael addition of aldehyde (via cyanohydrin if use -CN ascatalyst) to alpha, beta-unsaturated system.

 

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Stieglitz rearrangement

Stolle oxiindole synthesis

 Stork (Gilbert Stork 1921 - ) enamine reaction

 

Strecker (Adolph Friedrich Ludwig Strecker 1822-1871) amino acid synthesis

 Swern (Daniel Swern 1916 -1982) Oxidation is oxidation of alcohol to aldehyde or ketone under a mild condition (-78oC). Also, Pfitzner-Moffat Oxidation (DCC and DMSO), Corey-Kim Oxidation (NCS and DMS).

 

T

Tebbe olefination is the synthesis of alkene by using Tebbe's reagent. This reagent can be used in the methylenation of esters or amides for which the conventional Wittig reaction is not suitable. The driving force for this methylenation is the formation of titanocene oxide.

 Thorpe (Sir Jocelyn Field Thorpe 1872 - 1940) -Ziegler reaction

 

 Tiemann (Johann Carl Wilhelm Ferdinand Tiemann 1848-1899) rearrangement is the conversion of an oxime amide to urea.

 

 Tiffeneau (Marc Emile Pierre Adolphe Tiffeneau 1873 - 1945) -Demjanov (Nikolai Jakovlevich Demjanov) rearrangement

 

 Timmis pteridine synthesis

 

 Tschugaef olefination

 

U

Ugi (Ivar Karl Ugi 1930 - ) 4CC reaction is the nucleophilic addition of an isocyanide to an iminium ion, followed by another nucleophilic addition to give a stable alpha amino carboxamide. It is a multicomponent ( amino acid , imine and isocyanide) condensation, here we listed a special case of Ugi reaction, because Ugi  reaction mechanism is similar to that of Passierini reaction, you can change the ketone oxgen to imine amine group to get the result.

 

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V

 Vilsmeier (A. Vilsmeier) -Haack (A. Haack) reagent is the reagent formed with amide and POCl3, it is used in the acylation of alkene and aromatics.

 

Vinylether Rearrangement
Powell, S.G.; Adams, R. J. Am. Chem. Soc. 1920, 42, 646
Hurd, C.D.; Pollack, M.A. J. Org. Chem. 1939, 3, 550
Hill, H.S.; Pidgeon, L.M. J. Am. Chem. Soc. 1928, 50, 2718

Vinylogous Wolff rearrangement
Smith, A.B. III Chem. Commun. 1974, 695
Smith, A.B. III; Toder, B.H.; Branca, S.J. J. Am. Chem. Soc. 1976, 98, 7456
Branca, S.J.; Lock, R.L.; Smith, A.B. III J. Org. Chem. 1977, 42, 3165

W

 Wagner (Georg Egorovich Wagner 1849 - 1903) - Meerwein (Hans Meerwein 1879-1965) rearrangement

 

Wacker (Leonhard Wacker 1864 - 1936) Oxidation is the oxidation of the terminal alkene by palladium (II) to give the corresponding methyl ketone. The water addition intermediate undergoes the characteristic beta-elimination to generate the enol of  ketone.

 Wallach (Otto Wallach 1847 - 1921, Nobel Prize Chemistry 1910) rearrangement

 

 Wasserman-Bormann macrocyclic lactam synthesis

 

 Weinreb ketone synthesis

 

Wharton (Peter Stanley Wharton 1931 - ) reaction is the reduction of alpha, beta-epoxy ketone or alpha-halo ketone by hydrazine to allylic alcohol. The reaction proceeds by condensation of ketone and hydrazine to give enediimide intermediate.

 Wittig (georg F.K. Wittig 1897 - 1987 ) Olefin Synthesis. This reaction proceeds via intermediate called betaine and 4-membered ring transition state called oxaphosphetane. The reaction is not applicable to synthesis of highly hindered system. The normal Wittig reaction of nonstabilized ylides with aldehyde gives Z-olefins, but Schlosser modification gives E-Olefins.

 

 Wolff  (Ludwig Wolff 1857-1919)-Kishner (Nikolai Matveevič Kishner 1867-1935)-Huang Minlon reduction is a classic way to reduce ketone to methylene group. The only name reaction has a Chinese name.

 

 [2,3]-Wittig rearrangement

 

Wolff (Ludwig Wolff 1857 - 1919) rearrangement is the rearrngement of an alpha-diazo ketone. The carbene intermediate mechanism has been postulated. The migration group is known to migrate with retention of the configuration.

Y

Yamada coupling reagent is diethylphosphoryl cyanide that activates the acid to form amide bond, used a lot in peptide synthesis free of racemization.

 

 

Z

 Zinner hydroxylamine synthesis

 

 

Reactions Without Names

Aldehyde synthesis from epoxide

 

2-Aminothiazole synthesis

 

Bromine addition of double bond

 

Chlorination with POCl3 and tertiary amine.

 

Cyanation of Pyridine

 

Cyanation of Pyrrole

 

Demethyaltion with Lewis Acid

 

DMF catalyzed acid chloride synthesis

 

Grignard reduction

 

1-Hydroxybenzotriazole (HOBt) / DCC  amide formation mechanism

 

Hydoxyperoxide amide synthesis

 

Imidazolone synthesis

 

NIH Shift

 

Ninhydrin react with amino acids

 

Nitration of Benzene

 

Thiourea deprotection

 

t-BuLi Mechanism

 

 


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