Triplet (diphenoxyphosphory1)nitrene (3) was studied by solution phase laser flash photolysis, low-temperature absorption spectroscopy, and low-temperature EPR spectroscopy. In ethanol, an absorption maximum at 345 nm was observed upon laser flash photolysis of diphenyl phosphorazidate (1) and assigned to the triplet nitrene (z = 3.8 f 0.6 ps). After irradiation of 1 in an EPA glass at 77 K, an absorption attributed to the triplet nitrene was observed at 336 nm. The zero field splitting parameters from the EPR spectrum of the nitrene in EPA glass at 77 K were IDlhcl = 1.5408 cm-' and IElhcl = 0.007 39 cm-I. Stronger transient absorptions observed in hydroxylic solvents support the proposal that hydrogen bonding catalyzes intersystem crossing in nitrenes. [(a) Schuster, G. B.; Platz, M. S .
(Arenesulfonyl)hydrazone derivatives of aryl aldehydes
are readily alkylated by trialkylboranes in
the presence of base to generate new organoboranes that may be
converted to the corresponding
substituted alkanes or alcohols depending upon the reaction conditions
chosen. Both tosyl- and
trisylhydrazone derivatives can be utilized in the reaction, which
tolerates a variety of functional
groups, making it a versatile alternative to both the Grignard and
Suzuki-coupling reactions.
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