In Grignard reagent formation from cyclopropyl bromide in diethyl ether, trapping by DCPH is consistent with diffusing cyclopropyl radical intermediates.
[reaction: see text] For reactions of magnesium with cyclopropyl bromide in diethyl ether, added DCPH decreases the yield of cyclopropylmagnesium bromide by as much as 75%, while solvent-derived products disappear and cyclopropylcyclohexylphosphine and tetracyclohexyldiphosphine appear. These changes reflect trapping of diffusing intermediate cyclopropyl radicals.
Garst
J F
JF
Department of Chemistry, The University of Georgia, Athens 30602, USA. garst@chem.uga.edu
Ungváry
F
F
D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D005019:Ethyl Ethers / Q000737:chemistry*; D005609:Free Radicals; D010720:Phosphines / Q000737:chemistry; D012997:Solvents
D003521:Cyclopropanes; D005019:Ethyl Ethers; D005609:Free Radicals; D010720:Phosphines; D012997:Solvents