88875-34-7

Basic information

• Product Name: [1-Phenyl-1-pyrrolidin-1-yl-meth-(Z)-ylidene]-phosphoramidic acid diphenyl ester
• CAS NO: 88875-34-7
• Molecular Weight: 406.421
• Mol File: 88875-34-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [1-Phenyl-1-pyrrolidin-1-yl-meth-(Z)-ylidene]-phosphoramidic acid diphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [1-Phenyl-1-pyrrolidin-1-yl-meth-(Z)-ylidene]-phosphoramidic acid diphenyl ester(88875-34-7)
• EPA Substance Registry System: [1-Phenyl-1-pyrrolidin-1-yl-meth-(Z)-ylidene]-phosphoramidic acid diphenyl ester(88875-34-7)

Safety Data

• Hazardous Substances Data: 88875-34-7(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 26386-88-9 diphenyl phosphoryl azide 
• 98-86-2 acetophenone 
• 93-55-0 1-phenyl-propan-1-one 
• 148932-08-5 α-Pyrrolidino-β-methyl styrene 
• 58268-28-3 (E)-1-(1,2-diphenylvinyl)pyrrolidine 
• 94191-43-2 1-<1-phenyl-2-(2-pyridyl)-1-propenyl>pyrrolidine 
• 42353-58-2 1-(1,2-diphenyl-vinyl)-pyrrolidine 

Relevant articles and documents

DIPHENYL PHOSPHORAZIDATE (DPPA) AS A 1,3-DIPOLE. FORMATION AND DECOMPOSITION OF LABILE 1,2,3-TRIAZOLINE DERIVATIVES

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New Methods and Reagents in Organic Synthesis. 34. Diphenyl Phosphorazidate (DPPA) as a 1,3-Dipole. A Simple, Efficient Conversion of Alkyl Phenyl Ketones to 2-Phenylalkanoic Acids

Propiophenone (11) was conveniently converted to its enamines 12a-c using boron trifluoride etherate as a catalyst.Reaction of diphenyl phosphorazidate (DPPA) with the enamines 12a-c efficiently afforded the N-phosphorylated amidines 14a-c by the 1,3-dipolar cycloaddition of DPPA to the enamine double bond, followed by the evolution of nitrogen from the intermediate triazoline 13, and 1,2-migration of the phenyl group. 1,3-Dipolar elimination products 15a-c were also formed, though in very low yields.Some chemical properties of the N-phosphorylated amidine 14a, as well as the 1,3-dipolar character of DPPA, were investigated.By the same reaction sequences (enamine formation followed by the 1,3-dipolar cycloaddition of DPPA), some alkyl phenyl ketones 29a-c were conveniently converted to the N-phosphorylated amidines 31a, 31b, and 27 via the enamines 30a-c.However , in the case of acetophenone and its derivatives 33a-c, these reaction sequences proceeded sluggishly.Alkaline hydrolysis of the N-phosphorylated amidines 14a, 31a, 31b and 27 with potassium hydroxide afforded 2-phenylalkanoic acids 25 and 32a-c, respectively, in excellent yields.The overall three-step process of successive treatment of alkyl phenyl ketones (alkylmethyl) with pyrrolidine, DPPA, and potassium hydroxide may provide a new general method for the efficient conversion of alkyl aryl ketones to 2-arylalkanoic acids.Keywords - enamine; diphenyl phosphorazidate; boron trifluoride etherate; 1,3-dipolar cycloaddition; 1,2-migration; N-phosphorylated amidine; alkaline hydrolysis; alkyl aryl ketone; 2-arylalkanoic acid