17507-57-2

Basic information

• Product Name: Phosphine oxide, (diazophenylmethyl)diphenyl-
• CAS NO: 17507-57-2
• Molecular Formula: C19H15N2OP
• Molecular Weight: 318.315
• Mol File: 17507-57-2.mol

Chemical Properties

• CAS DataBase Reference: Phosphine oxide, (diazophenylmethyl)diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphine oxide, (diazophenylmethyl)diphenyl-(17507-57-2)
• EPA Substance Registry System: Phosphine oxide, (diazophenylmethyl)diphenyl-(17507-57-2)

Safety Data

• Hazardous Substances Data: 17507-57-2(Hazardous Substances Data)

Upstream product

• 4559-70-0 Diphenylphosphine oxide 
• 92-29-5 hydrobenzamide 
• 38031-27-5 (α-aminobenzyl)diphenylphosphine oxide 
• 588-68-1 1,2-di(benzylidene)hydrazine 
• 1499-21-4 Diphenylphosphinic chloride 
• 76202-74-9 N,N'-Bis-[(diphenyl-phosphinoyl)-phenyl-methyl]-C-phenyl-methanediamine 
• 2959-74-2 benzyldiphenylphosphine oxide 

Downstream Products

• 7751-69-1 α-chlorobenzyl(diphenyl)phosphine oxide 
• 52364-39-3 4-(α-Naphthyl)-2,3,3-triphenyl-1,2λ⁵-oxaphosphetan-2-on 
• 55860-88-3 4-(α-Methylstyryl)-2,2,3-triphenyl-1,2λ⁵-oxaphosphetan-2-on 
• 55911-54-1 4-(p-Methoxyphenyl)-2,3,3,6-tetraphenyl-3,4-dihydro-1,2λ⁵-oxaphosphorin-2-on 
• 55860-84-9 4-(4-methoxy-styryl)-2,3,3,4-tetraphenyl-[1,2]oxaphosphetane 2-oxide 
• 24665-54-1 4-(Diphenylmethylen)pyran 
• 2959-74-2 benzyldiphenylphosphine oxide 
• 76202-87-4 4-(p-Methoxyphenyl)-1,1-diphenyl-1,3-butadien 
• 4141-49-5 (Diphenylmethyl)diphenylphosphanoxid 
• 81431-85-8 3,3a-Dihydro-2,3,3-triphenyl-2H-cyclohept-1,2-oxaphosphol-2-oxid 
• 27949-47-9 1-(Diphenylmethylen)-4,5-benzocycloheptatrien 
• 78906-74-8 4-(p-Methoxyphenyl)-1,1,2-triphenyl-1,3-butadien 
• 55860-84-9 4-(p-Methoxy-styryl)-2,3,3,4-tetraphenyl-1,2-λ⁵-oxaphosphetan-2-on 
• 78906-76-0 2-Benzoyl-1-diphenylphosphoryl-3-(p-methoxyphenyl)-1-phenylcyclopropan 

Relevant articles and documents

Synthesis of β-Phosphinolactams from Phosphenes and Imines

Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.

Annulation of Diaryl(aryl)phosphenes and Cyclic Imines to Access Benzo-δ-phospholactams

Microwave-assisted annulation of cyclic imine dibenzo[b,f][1,4]oxazepines and diaryl(aryl)phosphenes generated from diazo(aryl)methyl(diaryl)phosphine oxides through the Wolff rearrangement accesses pentacyclic benzo-δ-phospholactams, 4b,16-dihydrodibenzo

Microwave-assisted periselective annulation of triarylphosphenes with aldehydes and ketones

The reaction of diazo(aryl)methyl(diaryl)phosphine oxides with aldehydes and ketones generates benzo-δ-phosphinolactones in low to good yields with 1,1-diarylalk-1-enes as byproducts under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo a Wolff rearrangement to form diaryl(aryl)phosphenes, which further react with aldehydes and ketones to afford benzo-δ-phosphinolactones and β-phosphinolactones. The latter are unstable under heating and fragment into the corresponding 1,1-diarylalk-1-enes and arylphosphine dioxides under reaction conditions. The arylphosphine dioxides become arylphosphonic acids during workup. The periselectivity in the annulation shows that the reaction of diaryl(aryl)phosphenes with most aldehydes and ketones favors phosphene phenyl participation in (4 + 2) annulation(2 + 2) annulation. This journal is

Carbenes, 22. Phosphenes: Trapping Reactions of (Diphenylmethylene)phenylphosphane Oxide by -Cycloaddition with Aldehydes

The photolysis of (diazobenzyl)diphenylphosphane oxide (5) in benzene yields the short-lived (diphenylmethylene)phenylphosphane oxide (15) via the carbene 12.The heterocumulene is trapped by aromatic aldehydes, which are added to the reaction mixture, in a -cycloaddition reaction with formation of the 1,2λ5-oxaphosphetanes 16a-e.Carbene reactions with the solvent (formation of the norcaradiene 13) as well as with the trapping reagents (formation of the C/H-insertion products 10a and b) cannot be avoided.With the α,β-unsaturated aldehydes 22a-c, the 1,2λ5-oxaphosphetanes 23a-c are primarily formed.They undergo a complete or a partial photofragmentation to the 1,3-butadienes 24a-c and phenylphosphane dioxide (25).