Triphenylphosphine diethyl

A very mild procedure for converting alcohols to iodides uses triphenylphosphine, diethyl azodicarboxylate (DEAD), and methyl iodide.24 This reaction occurs... [Pg.220]

Wang resin was purchased from Advanced ChemTech (1% DVB, 0.70mmol/g substitution, 100-200 mash, Cat. SA5009). Anhydrous tetrahydrofuran (THF), A/A-dimcthyl-formamide (DMF), methanol, dichloromethane, pyridine, 1,1 -carbonyldiimidazole (CDI), piperazine, homopiperazine, trans-1,4-diaminocyclohexane, 4-(dimethylamino)pyridine (DMAP), succinic anhydride, diglycolic anhydride, 3-methyl-glutaric anhydride, 2-aminophenol, 2-amino-p-cresol, 2-amino-4-tert-butyl phenol, /V-methylmorpholine (NMM), triphenylphosphine, diethyl azodicarboxylate (DEAD), and trifluoroacetic acid (TFA) were purchased from Aldrich Chemical Company, Inc. and used without further purification. PyBOP was purchased from Novabiochem. [Pg.80]

The role of the diethyl azodicarboxylate is to activate the triphenylphosphine toward nucleophilic attack by the alcohol. In the course of the reaction, the N=N double bond is reduced. As will be discussed subsequently, this method is applicable for activation of alcohols to attack by other nucleophiles in addition to halide ions. The activation of alcohols to nucleophilic attack by the triphenylphosphine-diethyl azodicarboxylate combination is called the Mitsunobu reaction. [Pg.146]

DEHYDRATION Copper(II) sulfate. Triphenylphosphine-Diethyl diazodi-carboxylate. [Pg.467]

Mitsunobu reaction Triphenylphosphine-Diethyl azodicar-boxylate, 44... [Pg.368]

Triphenylphosphine-Diethyl azodicar-boxylate-Lithium halides, 332 Mukaiyama aldol reaction 1-Methoxy-l, 3-bis(trimethylsilyloxy)-l, 3-butadiene, 178 Tin(II) chloride, 298 Titanium(IV) chloride, 304 Trityl perchlorate, 339 Murahashi reaction N,N-Methylphenylaminotributylphos-phonium iodide, 191... [Pg.368]

Triphenylphosphine-Diethyl azodi-carboxylate-Lithium halides, 332 by chloride... [Pg.374]

Triphenylphosphine-Diethyl azodi-carboxylate-Lithium halides, 332 by bromide Sodium bromide, 46 Tetraethylammonium bromide, 46 Triphenylphosphine-Diethyl azodi-carboxylate-Lithium halides, 332 by iodide Sodium iodide, 46 Sodium iodide-Boron trifluoride etherate, 282... [Pg.374]

Triphenylphosphine-Diethyl azodicar-boxylate, 332 Other substitutions Allyltrimethylsilane, 11 Benzylamine, 79 Bromodimethylborane, 47 Chlorotrimethylsilane-Lithium, 81 Crotyltrimethylsilane, 86 Diethylzinc-Titanium(IV) chloride, 21 Lithium bis(dimethylphenylsily 1)-cuprate, 161... [Pg.375]

General methods from alcohols Triphenylphosphine-Diethyl azodicar-boxylate-Lithium halides, 332 Alkyl fluorides... [Pg.382]

Diethoxytriphenylphosphorane, 109 Diphosphorus tetraiodide, 127 Phenyl azide-Aluminum chloride, 240 Triphenylphosphine-Diethyl azodicar-boxylate, 332... [Pg.384]

Aluminum chloride, 15 Palladium catalysts, 230 N-Phenylselenophthalimide, 245 Containing one nitrogen, one oxygen—oxazolines Potassium bicarbonate, 253 Triphenylphosphine-Diethyl azodi-carboxylate, 332... [Pg.390]

LACTAMS Benzenesulfenyl chloride. Pentacarbonyl(methoxyalkyl)chromium carbenes. Triphenylphosphine-Diethyl diazodicarboxylate. [Pg.651]

Mitsunobu conditions [triphenylphosphine/diethyl azodicarboxylate (DEAD)]7 and triphenylphosphite methiochde [(PhO)3P+MeI ] or dihalides [(PhO)3P + XX-j8 have been successfully applied to the synthesis of halogeno sugars. [Pg.57]

INVERSION, OF ALCOHOLS Cesium propionate. Triphenylphosphine-Diethyl azodicarboxylate. [Pg.661]

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