Sodium 2-methyl-2-butoxide

Bases, strong Choline. Claisen s alkali. Lithium (potassium, sodium) amide (ethoxide, hydroxide, methoxide). Lithium nitride. Phenyllithium (potassium, sodium). Potassium r-butoxide. Potassium (sodium) 2-methyl-2-butoxide. Resins Amberlite IRA-dOO. Dowex... 

C-Alkylation Diethyl sulfate. Dimethyl sulfate. Dimethyl sulfoxide reagent (a). Methyl bromide. Methyl chloride. Nitrosonium hexafluorophosphate. Potassium r-butoxide. Sodium amide, Sodium ethoxide. Sodium 2-methyl-2-butoxide. Tetramethylurea. Tri-ethyloxonlum fluuruburate. Trimcthyloxonium fluurubomte. Trimethyloxonium 2,4,6-trlnltrobenzene lulfonale. Triiyliodium. 

Bases Alumina, see p-Toluenesulfonylhydrazine. Dehydroabietylamine. 1,5-Diazabicyclo [4.3.0]nonene-5. 1,4-Diazabicyclo[2.2.2]octane. l,S-Diazabicyclot5.4.0]undecene-5. 2,6-Di-/-butylpyridine. N,N,-Diethylglycine ethyl ester, see /-Amyl chloroformate. 2,6-Dimethyl-piperidine. Ethanolamine. Lithium diisopropylamide, see Diphenylsulfonium isopropylide. Lithium nitride. Magnesium methoxide. N-Methylmorpholine. Piperidine. Potassium amide. Potassium hydroxide. Potassium triethylmethoxide. Pyridine. Pyrrolidine. Sodium methoxide. Sodium 2-methyl-2-butoxide. Sodium thiophenoxide. Thallous ethoxide. Triethyla-mine. Triphenylphosphine, see l-Methyl-2-pyrrolidone. 

Wittig reactions Carbomethoxymethylenetriohenylphosphorane. Cyclopropyltriphenyl-phosphonium bromide. l,5-Diazabicyclo[4.3.0]nonene-5. Diethyl cyanomethylphosphonate. p-Diphenylphosphinobenzoic acid. Diphenylsulfonium isopropylide. Diphenyl triphenyl-phosphoranylidenemethylphosphonate. Ethyl(dimethylsulfuranylidine)acetate. Ethylene oxide. Hexamethylphosphorous triamide. Methoxymethylenetriphenylphosphorane. Meth-ylenemagnesium bromide (chloride). Simmons-Smith reagent. Sodium 2-methyl-2-butoxide. 

Sodium hydroxide, 158 Sodium hypobromite, 383-384 Sodium hypochlorite, 67 Sodium iodide, 166, 384, 461 Sodium isopropoxide, 385 Sodium-lead alloy, 385 Sodium methoxide, 223, 385-386, 418 Sodium 2-methyl-2-butoxide, 138, 386 Sodium methyl phosphorazidate, 386 Sodium methylsulfinylmethide, 130, 166-169, 284... 

REARRANGEMENTS, RAMBERG-BACKLUND Sodium 2-methyl-2-butoxide. 

On treatment with sodium ethoxide in ethanol, methyl 2,4,6-tri-O-methyl-a- (72) and -/3-D-ribo-hexosid-3-ulose yielded l-deoxy-2-methoxy-4,6-di-0-methyl-D-hex-l-en-3-ulose (73) and several isomeric ethyl 2,3,6-tri-0-methylhexosid-3-uloses (74) (see Scheme 10).133 On alkaline degradation of methyl 2,3-di-0-ethyl-6-0-pro-pyl-a-D-xy/o-hexosid-4-ulose (75) with sodium 1-butoxide in 1-butanol, one mole of ethanol was released per mole of 75, indicating that the substituent at C-2 was preferentially eliminated. On mild, acid hydrolysis of the product, methanol, ethanol, and some 1-propanol were formed, consistent with fission at C-l, C-3, and, to some extent, C-6 (see Scheme 10).134... 

Rendleman have shown that the monosodium alcoholate of methyl a-D-glucopyranoside can also be obtained by treatment of the D-glucoside with sodium 1-butoxide in boiling 1-butanol (reaction 5). Heat is probably not... 

In a refluxing solution of sodium hydroxide and methyl a-D-glucopyranoside in 1-butanol, possibly both the hydroxide ion and the butoxide ion react directly with the D-glucoside to produce an alcoholate. Sodium 1-butoxide is formed readily, in quantitative yield, by refluxing a solution of sodium hydroxide in an excess of 1-butanol (reaction 6) under dry... 

The product isolated from the reaction of methyl a-D-glucopyranoside with either sodium hydroxide or sodium 1-butoxide in refluxing 1-butanol... 

Shibasaki made several improvements in the asymmetric Michael addition reaction using the previously developed BINOL-based (R)-ALB, (R)-6, and (R)-LPB, (R)-7 [1]. The former is prepared from (R)-BINOL, diisobutylaluminum hydride, and butyllithium, while the latter is from (R)-BINOL, La(Oz -Pr)3, and potassium f-butoxide. Only 0.1 mol % of (R)-6 and 0.09 mol % of potassium f-butoxide were needed to catalyze the addition of dimethyl malonate to 2-cy-clohexenone on a kilogram scale in >99% ee, when 4-A molecular sieves were added [15,16]. (R)-6 in the presence of sodium f-butoxide catalyzes the asymmetric 1,4-addition of the Horner-Wadsworth-Emmons reagent [17]. (R)-7 catalyzes the addition of nitromethane to chalcone [18]. Feringa prepared another aluminum complex from BINOL and lithium aluminum hydride and used this in the addition of nitroacetate to methyl vinyl ketone [19]. Later, Shibasaki developed a linked lanthanum reagent (R,R)-8 for the same asymmetric addition, in which two BINOLs were connected at the 3-positions with a 2-oxapropylene... 

Sodium 2-Methyl-2-propoxide, see Sodium fert-butoxide, 1661b... 

Di-tert,-butylphosphino)-biphenyl has been used by Buchwald [5] et al. as the most efficient ligand in the Pd-catalyzed amination of aryl chlorides. 2-Chloro-4-methyl-toluene can be aminated with pyrrolidine in 98% yield using sodium-tert.-butoxide [eq. (e)]. 

Explosive reaction with sodium -I-methanol or sodium methoxide + methanol. Mixtures with sodium or potassium are impact-sensitive explosives. Reacts violently with acetone + alkah (e.g., sodium hydroxide, potassium hydroxide, or calcium hydroxide), Al, disilane, Li, Mg, methanol + alkah, nitrogen tetroxide, perchloric acid + phosphorus pentoxide, potassium-tert-butoxide, sodium methylate, NaK. Incompatible with dinitrogen tetraoxide, fluorine, metals, or trhsopropylphosphine. Nonflammable. When heated to decomposition it emits toxic fumes of CT. 

Although potassium fert-butoxide (f-BuOK), sodium methylate (NaOCHs), sodium ethylate (NaOC2H5), alcoholic potassium hydroxide, and sodium hydroxide solutions have been used, the utilization of the... 

This discussion of aliphatic carbanion structures has included mainly organolithium compounds simply because the structures of most aliphatic caibanions incorporate lithium as the counterion and also because this alkali metal cation is the most widely used by synthetic organic chemists. For comparison the entire series of Group la methyl carbanion structures, i.e. MeNa, MeK, MeRb and MeCs, have been determined. Methylsodium was prepared by reaction of methyllithium with sodium r-butoxide. Depending upon the reaction conditions, the products obtained by this procedure contain variable amounts of methyllithium and methylsodium (Na Li atom ratios from 36 1 to 3 1). Hie crystal structure of these methylsodium preparations resembles the cubic tetramer (38) obtained for methyllithium with the Na— Na distances of 3.12 and 3.19 A and Na—C distances of 2.58 and 2.64 A. 

The structural problem remains unsolved, but as dihydrocodeinones can be converted into dihydrothebaines by sodium tertiary butoxide and methyl sulphate, it is possible that the problem will receive a solution by the degradation of methyl- and isomethyldihydrothebaines in a manner similar to the degradation of dihydrothebaine to [xvii] or [xvm] [13-14] (see Chap. XIII). 

Sodium tert-butoxide tert-Butyl alcohol, sodium salt (8) 2-Propanol, 2-methyl-, sodium salt (9) (865-48-5)... 

Sodium ferf-butoxide in N,N-dimethylformamide at KXP was found to be very effective in promoting intramolecular displacements408 and 2,5 -anhydrothymidine was obtained directly from 5 -0-(methyl-sulfonyl)thymidine with these reagents. The same conditions have also been used to synthesize the anhydronucleosides 121 and 122 from a pseudouridine derivative408 and from a D-ribosyl derivative of 2,4-quinazolinedione.410 The same reagents with 3 -0-p-tolylsulfonyl-uridine gave mainly 1 -(2,3 -anhydro-y3-D-xylofuranosyl)uracil.408... 

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