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Pyrolysis of aryl azides. II. Naphthyl azides

Authors: P. R. Sadler; L. K. Dyall; G. Boshev;

Pyrolysis of aryl azides. II. Naphthyl azides

Abstract

Kinetic studies of the pyrolyses of 1- and 2-naphthyl azides reveal neighbouring group participation by nitro and phenylazo substituents. The acceleration observed in 1-nitro-2-naphthyl azide, 1-phenylazo-2-naphthyl azide, and 2-nitro-1-naphthyl azide is 1730-, 211-, and 23.6-fold, respectively, in nitrobenzene solution at 120�. These effects are all smaller than that of the 2-nitro group in phenyl azide (3370-fold), which is ascribed to the steric effect of the peri hydrogen at C8 in naphthyl azides. The sizes of these neighbouring group effects correlate with the success of oxidative cyclization of ortho-substituted naphthylamines with (diacetoxyiodo)benzene.

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
12
Average
Top 10%
Average
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