N-heterocyclic superelectrophiles and evidence for single electron transfer chemistry.
In reactions with benzene and related substrates, an oxazole-based superelectrophile is found to be significantly more reactive than a related monocationic species. Theoretical calculations estimate that the lowest unoccupied molecular orbital (LUMO) for the superelectrophile is about 4 eV lower in energy than the LUMOs of comparable monocations. When the oxazole-based superelectrophile is reacted with ferrocene, a dimeric product is formed in high yield. The dimerization occurs by a single electron transfer reaction between the dicationic superelectrophile and ferrocene, followed by coupling of the radical cations.
Sai
Kiran Kumar Solingapuram
KK
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Tokarz
Matthew J
MJ
Malunchuk
Andrew P
AP
Zheng
Chong
C
Gilbert
Thomas M
TM
Klumpp
Douglas A
DA