Year: 2025
Type: article
Abstract: Although sigmatropic rearrangements have been widely reported, nitro group shifts have rarely been investigated. In this study, we investigated the synthesis of 4-ethoxycarbonyl-2-nitrophenols via the [1,3]-nitro shift. 4-Ethoxycarbonyl-4-nitrocyclohexanone, when subjected to I2–DMSO system, gave the 4-nitrocyclohexa-2,5-dienenone intermediate that undergoes [1,3]-nitro shift followed by aromatization to afford 4-ethoxycarbonyl-2-nitrophenols. Although there is a room for improvement in product yield and selectivity, the development of a reaction system that facilitates [1,3]-nitro shift from readily available starting materials is noteworthy.
Source: Journal of Oleo Science
DOI: 10.5650/jos.ess25139
Authors: Kento Iwai, Takumi Hamada, Nagatoshi Nishiwaki
Institutions: Kochi University of Technology, Nara Women's University
Language: English
Topic: Chemical Reaction Mechanisms
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $301
OpenAlex ID: W4414639753