Bromo–nitro substitution on a tertiary α carbon—a previously uncharacterized facet of the Kornblum substitution

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 N 1/S N 2 mechanism domain for Kornblu...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2015-01, Vol.5 (93), p.76401-76418
Main Authors: Leonard, Matthew J., McKay, Peter G., Lingham, Anthony R.
Format: Article
Language:English
Subjects:
Amides
Bromine
Carbonyls
Sodium nitrite
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 N 1/S N 2 mechanism domain for Kornblum substitutions.
ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA14798K