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*  Diazomethane
... is also frequently used as a carbene source. It readily takes part in 1,3-dipolar cycloadditions. Diazomethane is ... MSDS diazomethane CDC - NIOSH Pocket Guide to Chemical Hazards Sigmaaldrich technical bulletin (PDF) Sigma-Aldrich diazomethane ... Many substituted derivatives of diazomethane have been prepared: Diazomethane is both isomeric and isoelectronic with the more ... In the Büchner-Curtius-Schlotterbeck reaction diazomethane reacts with an aldehyde to form ketones. When diazomethane reacts ...
*  Büchner-Curtius-Schlotterbeck reaction
An acyl-diazomethane can react with an aldehyde to form a β-diketone in the presence of a transition metal catalyst (SnCl2 in ... Acyl-diazomethane can also add to esters to form β-keto esters, which are important for fatty acid synthesis. As mentioned ... For example, an acyl-diazomethane can react with an aldehyde in the presence of a DBU catalyst to form isolable α-diazo-β- ... THE ACTION OF DIAZOMETHANE ON CERTAIN DERIVATIVES OF α-PYRONE". Journal of Organic Chemistry. 6 (4): 577-583. doi:10.1021/ ...
*  1,3-Dipolar cycloaddition
For example, the reactivity scale of diazomethane against a series of dipolarophiles is shown in the scheme below. Diazomethane ... The carbon of diazomethane bears the largest HOMO orbital, while the terminal olefinic carbons of methyl acrylate and styrene ... For example, diazomethane bears the largest negative character at the terminal nitrogen atom, while hydrazoic acid bears the ... For example, diazomethane generally adds to methyl acrylate to give 3-carboxyl pyrazoline. However, by putting more steric ...
*  Trimethylsilyldiazomethane
Although less likely to explode than diazomethane, trimethylsilyldiazomethane may be just as toxic. Inhalation of diazomethane ... It also reacts with alcohols to give methyl ethers, where diazomethane may not. It has also been employed widely in tandem with ... Trimethylsilyldiazomethane, (CH3)3SiCHN2, is a diazo compound widely used as a less-explosive replacement for diazomethane. ... It is a less explosive alternative to diazomethane for the methylidenation of carboxylic acids. ...
*  Thermal runaway
Lowe, Derek (2008-04-30). "How Not To Do It: Diazomethane". Science Translational Magazine. American Association for the ...
*  Pentacarbonylhydridomanganese
This compound can be methylated with diazomethane. HMn(CO)5 + CH2N2 → Mn(CO)5CH3 + N2 Eley, D.D.; Pines, Herman; Weisz, P.B. ...
*  Cyclobutanone
A newer, more efficient preparation of cyclobutanone was found by P. Lipp and R. Köster in which a solution of diazomethane in ... The reaction mechanism was confirmed by a reaction using 14C-labeled diazomethane. Another method for the synthesis of ... Radioactive Cyclobutanone from Ketene and Diazomethane-14C1". Journal of the American Chemical Society. 78 (13): 3221-3223. doi ...
*  Maximilian Nierenstein
Geake, A.; Nierenstein, M. (1914). "The Action of Diazomethane on Caseinogen: Preliminary Communication". The Biochemical ... an organic reaction describing the conversion of an acid chloride into an haloketone with diazomethane. In 1912, Polish ...
*  Arndt-Eistert reaction
Since diazomethane is toxic and violently explosive, many safer alternatives have been developed, such as the usage of ynolates ... Acid chlorides react with diazomethane to give diazoketones. In the presence of a nucleophile (water) and a metal catalyst ( ... In the Newman-Beal modification, addition of triethylamine to the diazomethane solution will avoid the formation of α- ... is that the methylene group alpha to the carboxyl group in the product is the methylene group from the diazomethane reagent. It ...
*  Nierenstein reaction
If excess diazomethane is present during the reaction, it can act as a base, abstracting a hydrogen from the diazonium-salt ... It is an insertion reaction in that the methylene group from the diazomethane is inserted into the carbon-chlorine bond of the ... 26, p.13 (1946). (Article) M. Nierenstein; D. G. Wang & J. C. Warr (1924). "The Action of Diazomethane on some Aromatic Acyl ... H. H. Lewis; M. Nierenstein & Enid M. Rich (1925). "The Action of Diazomethane on some Aromatic Acyl Chlorides III. The ...
*  Wolff rearrangement
The Arndt-Eistert reaction involves the acylation of diazomethane with an acid chloride, to yield a primary α-diazo ketone. The ... Thus, triethylamine or a second equivalent of diazomethane must be added to scavenge the HCl produced in order to prevent ... The acid chloride then reacts with diazomethane (R2 = H), or occasionally a diazoalkyl, via the Arndt-Eistert procedure, to ... CS1 maint: Multiple names: authors list (link) Clibbens, D. A. Nierenstein, M. (1915). "CLXV.-The action of diazomethane on ...
*  Diazo
The simplest example of a diazo compound is diazomethane. The electronic structure of diazo compounds involves a positive ... such as in the synthesis of diazomethane from Diazald or MNNG: Hydrazones are oxidized (dehydrogenation) for example with ... of an electrophilic substitution using a diazomethyl compound is that of a reaction between an acyl halide and diazomethane, ...
*  Insertion reaction
3.0.CO;2-D. Clibbens, D. A.; Nierenstein, M. (1915). "The Action of Diazomethane on some Aromatic Acyl Chlorides". J. Chem. Soc ... Nierenstein, M.; Wang, D. G.; Warr, J. C. (1924). "The Action of Diazomethane on some Aromatic Acyl Chlorides II. Synthesis of ... Consequently, the methylene group α- to the carboxyl group in the product is the methylene group from the diazomethane reagent ... Lewis, H. H.; Nierenstein, M.; Rich, E. M. (1925). "The Action of Diazomethane on some Aromatic Acyl Chlorides III. The ...
*  Buckminsterfullerene
Cyclopropanation also occur readily with diazomethanes. For example, diphenyldiazomethane reacts readily with C60 to give the ...
*  11-Deoxycorticosterone
Reaction of that acid halide with diazomethane gives the diazoketone (). The hydroxyl group at C3 is then oxidized to the ...
*  N-Nitroso-N-methylurea
NMU is the traditional precursor in the synthesis of diazomethane. However, because it is unstable at temperatures beyond 20 °C ...
*  Telluric acid
Reaction with diazomethane gives the hexamethyl ester, Te(OMe)6. Telluric acid and its salts mostly contain hexacoordinate ...
*  Bingel reaction
An alternative to the Bingel reaction is a fullerene diazomethane reaction. N-(Diphenylmethylene)glycinate Esters in a Bingel ...
*  Demjanov rearrangement
I. Diazomethane and Tiffeneau-Demjanov ring expansions of norcamphor and dehydronorcamphor". J. Org. Chem. 38 (23): 4059. doi: ... Diazomethane also produces ring enlargement, and its reaction is mechanically similar to the Tiffeneau-Demjanov rearrangement. ... Jones, J.B.; Price, P. (1973). "Steroids and steroidases-XIX: Comparison of diazomethane and tiffeneau-demjanov homologations ... Evidence for predominant equatorial approach of the C-3 carbonyl group by diazomethane". Tetrahedron. 29 (14): 1941-1947. doi: ...
*  Nucleophilic acyl substitution
Alternatively, diazomethane can be used to convert an acid to an ester. While esterification reactions with diazomethane often ... give quantitative yields, diazomethane is only useful for forming methyl esters. Thionyl chloride can be used to convert ...
*  Carbene
For example, the reaction of methylene generated from photolysis of diazomethane with cis-2-butene or with trans-2-butene each ... To generate an alkylidene carbene a ketone can be exposed to trimethylsilyl diazomethane. Carbenes and carbenoid precursors can ... In 1912 Hermann Staudinger also converted alkenes to cyclopropanes with diazomethane and CH2 as an intermediate. Doering in ...
*  Melengestrol
Reaction with diazomethane at the conjugated double bond at 16 gives first the pyrazole (6). This heterocycle affords the 16 ...
*  Simmons-Smith reaction
Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The ...
*  Cycloheptanone
... is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source. Cycloheptanone ...
*  Cyclopropanation
Certain diazo compounds, such as diazomethane, can react with olefins to produce cyclopropanes in a 2 step manner. The first ... Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The ...