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Kinetics of the thermal decomposition of ferrocenyl azide: Character of ferrocenyl nitrene

✍ Scribed by C. Steel; M. Rosenblum; A. S. Geyh

Book ID
102928049
Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
658 KB
Volume
26
Category
Article
ISSN
0538-8066

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✦ Synopsis

The Arrhenius parameters for the thermal decomposition of ferrocenyl azide in isooctane are A = (5.1 2 1.4) X 10l2 s-l and Eact = 113.1 2 0.9 (kJ mol-l) and the rate is relatively insensitive to solvent (isooctane, benzene, acetonitrile: 1:1.7:2.4). The results indicate a relatively nonpolar transition state which is considerably "tighter" than for a normal bond fission reaction. The Arrhenius parameters are comparable to those for aromatic azides and do not offer any support for anchimeric assistance by the iron atom. A kinetic scheme is presented which accounts for the observed products: Nitrogen, ferrocene, aminoferrocene, azoferrocene, and insoluble material. Rates of hydrogen abstraction by the intermediate ferrocenyl nitrene from cyclohexane, benzene, and acetonitrile are used to show that the nitrene is nucleophilic.

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