Bromo-nitro substitution on a tertiary α carbon - A previously uncharacterized facet of the Kornblum substitution

Leonard, M, McKay, P and Lingham, A 2015, 'Bromo-nitro substitution on a tertiary α carbon - A previously uncharacterized facet of the Kornblum substitution', RSC Advances, vol. 5, no. 93, pp. 76401-76418.


Document type: Journal Article
Collection: Journal Articles

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Title Bromo-nitro substitution on a tertiary α carbon - A previously uncharacterized facet of the Kornblum substitution
Author(s) Leonard, M
McKay, P
Lingham, A
Year 2015
Journal name RSC Advances
Volume number 5
Issue number 93
Start page 76401
End page 76418
Total pages 18
Publisher Royal Society of Chemistry
Abstract Sodium nitrite in dimethylformamide substitutes nitro for bromine alpha to an amide carbonyl in high yield at a tertiary site. Hammett plots show a strongly positive ρ value (+0.67), indicating a negatively-charged transition state, in contrast to the typical S<inf>N</inf>1/S<inf>N</inf>2 mechanism domain for Kornblum substitutions. 2015
Subject Macromolecular and Materials Chemistry not elsewhere classified
DOI - identifier 10.1039/c5ra14798k
Copyright notice © The Royal Society of Chemistry 2015
ISSN 2046-2069
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