58477-00-2

Upstream product

• 111680-13-8 C₁₈H₁₈N₄O₈S₂ 
• 603-35-0 triphenylphosphine 
• 1972-28-7 diethylazodicarboxylate 

Downstream Products

• 83664-96-4 C₃₀H₂₁Cl₄O₂P 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 791-28-6 Triphenylphosphine oxide 
• 83664-97-5 di-n-butoxytriphenylphosphorane 
• 105785-75-9 bis(neopentyloxy)triphenylphosphorane 
• 111680-13-8 C₁₈H₁₈N₄O₈S₂ 
• 17663-89-7 diphenoxytriphenylphosphorane 
• 83664-98-6 diisopropoxytriphenylphosphorane 
• 1706-96-3 phenyl diphenylphosphinate 
• 88194-93-8 diethyl N-(3-benzylaminopropyl)hydrazodicarboxylate 

Relevant academic research and scientific papers

The Mechanism of the Mitsunobu Azide Modification and the Effect of Additives on the Rate of Hydroxyl Group Activation

The Mitsunobu azide modification has been studied by NMR using a hindered alcohol and the principle intermediates involved have been tentatively identified.The accelerated hydroxyl group activation in the presence of hydrazoic acid or of catalytic quantities of phenol gives us an insight into the reactivity of some of the intermediates involved in these reactions.

Mechanism of regioselective Mitsunobu thiofunctionalization of pentofuranoses

Triphenylphosphine and diethyl azodicarboxylate react with 1,2-O-isopropylidene-α-D-xylo-(1) and ribofuranose (2) to give six-membered-ring phosphoranes. Xylofuranose 1 undergoes cyclodehydration to produce oxetane 17 in 85% yield, but ribofuranose 2 give

Electrophilic reactivities of azodicarboxylates

The kinetics of the reactions of the azodicarboxylates 1 with the enamines 2 have been studied in CH3CN at 20 °C. The reactions follow a secondorder rate law and can be described by the linear free energy relationship logk2(20 °C) =

Structure of the radicals formed in the Mitsunobu reaction

The first step of the Mitsunobu reaction consists of the reaction between a dialkyl azodicarboxylate (1) and triphenylphosphine (2) with formation of a phosphobetaine, ROOCN(P+Ph3)N-COOR (3). It was recently observed by EPR spectroscopy that a low concentation of a radical accompanied 3, and its structure was assigned to the product of one-electron oxidation of 3, the distonic radical cation ROOCN(P+Ph3)NCOOR (4), based on EPR spectral evidence. [Camp. D., Hanson, G. R. and Jenkins, I. D. J. Org. Chem. 60 (1995) 2477.] A study of 3 and similar betaines by cyclic voltammetry revealed that 3 is far too difficult to oxidize (Epa was around 2.0 V vs. Ag/AgCl) to be a credible precursor of the radical species. In combination with an EPR spectral study of a series of 1-R3P reactions results have been obtained which suggest that the radical species instead is derived from a structure in which the phosphorus atom is connected to the carbonyl oxygen of 1, i.e. (Ph3P+O)(RO)C=N-NCOOR. The reaction between 2 and 4-phenyl-4H-1,2,4-triazolinedione (PTAD) produced similar radical species, indicating that radical cation species derived from the cyclization of 4 (P to the carbonyl oxygen) cannot be involved. Acta Chemica Scandinavica 1998.

REACTION OF DIARYL DISULFIDES WITH N-CHLOROBENZENECARBOXIMIDIC AND N-CHLOROCARBONIMIDIC ESTERS

Diaryl disulfides and alkyl N-chlorobenzenecarboximidates react in a molar ratio of 1:2 with the formation of alkyl N-(arylthio)benzenecarboximidates and N-benzoylarenesulfinimidoyl chlorides.The reaction of diaryl disulfides with ethyl N-chlorocarbonimidate gives N,N'-bis(arylthio)-N,N'-bis(ethoxycarbonyl)hydrazines.

ALKYL HALIDES FROM ALCOHOLS: AN EFFECTIVE METHOD UNDER MILD CONDITIONS

Primary alkyl chlorides and bromides are obtained from the carbinol precursors and an organic amine hydrohalide under straightforward Mitsunobu conditions.

A Novel Phosphorus -> Oxygen Phenyl Migration: Triphenylphosphine Dioxide as a Reaction Intermediate

Treatment of triphenylphosphine with diethyl azodicarboxylate and hydrogen peroxide results in the formation of phenyl diphenylphosphinate; triphenylphosphine dioxide is suggested as an intermediate.