122424-80-0

Basic information

• Product Name: (1R,4S,5S,6S)-3,4-Dimethyl-2,5,6-triphenyl-1-phospha-bicyclo[2.2.1]hept-2-ene
• CAS NO: 122424-80-0
• Molecular Weight: 368.458
• Mol File: 122424-80-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,4S,5S,6S)-3,4-Dimethyl-2,5,6-triphenyl-1-phospha-bicyclo[2.2.1]hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,5S,6S)-3,4-Dimethyl-2,5,6-triphenyl-1-phospha-bicyclo[2.2.1]hept-2-ene(122424-80-0)
• EPA Substance Registry System: (1R,4S,5S,6S)-3,4-Dimethyl-2,5,6-triphenyl-1-phospha-bicyclo[2.2.1]hept-2-ene(122424-80-0)

Safety Data

• Hazardous Substances Data: 122424-80-0(Hazardous Substances Data)

Upstream product

• 645-49-8 cis-stilben 
• 30540-36-4 3,4-dimethyl-1-phenylphosphole 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Downstream Products

• 122424-85-5 2,5-endo,6-exo-triphenyl-3,4-dimethyl-1-phosphabicyclo<2.2.1>hept-2-ene P-oxide 

Relevant articles and documents

Cycloadditions between 2H-Phospholes and Alkenes. Synthesis and Properties of 1-Phosphanorbornenes

2H-Phospholes, obtained by isomerization of 1H-phospholes at ca. 150 deg C, achieve cycloadditions with disubstituted alkenes to yield 1-phosphanorbornenes.In the case of symmetrical (E)-alkenes, α-exo,β-endo compounds are formed predominantly or even exclusively.Spectral assignments of these compounds are checked by an X-ray structure determination.The 1-phosphanorbornenes formed by reacting 2H-phospholes and (Z)-alkenes undergo an epimerization and then give the same products as (E)-alkenes do.The study of the evolution of the reaction mixture shows that the cycloaddition should proceed via a concerted mechanism followed by a cleavage of the newly formed P-C single bond.Regioselectivity of nonsymmetrical alkenes is controlled by the steric hindrance of the phosphole moiety.The transient phosphadiene exhibits a rather high reactivity toward dienophiles and the presence of an alcoholic function does not disturb the cycloaddition.