SbF(5)-mediated reactions of oxafluorodiazirines.
[reaction: see text] The reaction of benzyloxyfluorodiazirine (3) with SbF(5) in benzene gives PhCH(2)OCF, which undergoes SbF(5)-mediated fragmentation to PhCH(2)(+), CO, and SbF(6)(-); the benzyl cation alkylates benzene to yield diphenylmethane. Phenoxyfluorodiazirine (4) reacts with SbF(5) in benzene to give PhOCF and (ultimately) triphenylmethane by a pathway that avoids fragmentation.
Moss
R A
RA
Department of Chemistry, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu
Fedé
J M
JM
Yan
S
S
D000965:Antimony / Q000737:chemistry*; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008958:Models, Molecular
D006845:Hydrocarbons, Fluorinated; D003978:Diazomethane; D000965:Antimony; D005459:Fluorides