p-Substituted 1-chloro-3-phenyldiazirines (5), the putative intermediates of the reaction of N,N,N′-trichlorobenzamidines (10) with excess of bromide ions, react further to afford mixtures of 3-bromo- (4) and 3-chloro-3-phenyldiazirines (6). The 6:4 ratio
Martinu, Tomas,Dailey, William P.
p. 5012 - 5015
(2007/10/03)
Dimerization and trapping of diazirinyl radicals
Computational and experimental methods have been utilized to examine the facile dimerization of diazirinyl radicals. Two potential dimers were investigated using density functional theory. Both were shown to have low-barrier reaction coordinates leading t
Thompson, Robert A.,Francisco, Joseph S.,Grutzner, John B.
p. 756 - 765
(2007/10/03)
EQUILIBRIUM CONSTANTS FOR TRIPHENYLMETHYL BROMIDE AND 3-BROMO-3-PHENYLDIIRINE IN ACETONITRILE
The equilibrium constatns at 25 deg C are 7.6E-3 and 2.0E-5 for triphenylmethyl bromide and bromidazirine respectively.
Liu, Michael T. H.,Paike, N.
p. 3763 - 3766
(2007/10/02)
AZIDE AND FLUORIDE EXCHANGE REACTIONS OF HALODIAZIRINES
Reactions of 3-aryl-3-bromodiazirines (11) with molten tetrabutylammonium fluoride at 25degC provide 65-74percent isolated vields of the novel corresponding 3-aryl-3-fluorodiazirines (12) Related reactions of 11 with tetrabutylammonium azide afford high yields of aryl nitriles.The latter reactions are believed to proceed through unstable intermediate 3-aryl-3-azidodiazirines (7).These reactions involve rate-determining formation of 7 and display kinetics which are first order in azide ion and bromodiazirine.The likely intermediacy of aryldiazirinium bromide ion pair between 11 and 7 is supported by a combination of salt effect, leaving group effect and Hammett studies.Molecular orbital calculations are employed to characterize azidodiazirines as well as the mode of their decomposition to nitriles.In particular, we consider the possible itermediacy of a 3-nitrenodiazirine or an azidocarbene.
Moss, Robert A.,Terpinski, Jacek,Cox, D. Phillip,Denneey, Dorothy Z.,Krogh-Jespersen, Karsten
p. 2743 - 2748
(2007/10/02)
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