Unprecedented chemistry of an aryloxychlorodiazirine: generation of a dihalodiazirine and diazirinone.
The reaction of p-nitrophenoxychlorodiazirine with tetrabutylammonium fluoride follows three channels: (1) approximately 17% of p-nitrophenoxide/fluoride exchange to chlorofluorodiazirine and p-nitrophenol, (2) approximately 28% of Cl/F exchange to p-nitrophenoxyfluorodiazirine, and (3) approximately 55% of ipso fluoride attack, affording p-nitrofluorobenzene and the previously unknown diazirinone (diazacyclopropenone).
Moss
Robert A
RA
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu
Chu
Gaosheng
G
Sauers
Ronald R
RR