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Synthetic Approach to the Preparation of (2-Acetoxy)allyl Nitro Compounds

Author:
Gabrielli, Serena, Mariotti, Nicole, Chiurchiù, Elena, Ballini, Roberto, Petrini, Marino, Palmieri, Alessandro
Source:
Journal of organic chemistry 2018 v.83 no.20 pp. 12855-12862
ISSN:
1520-6904
Subject:
acetaldehyde, acetylation, alcohols, moieties, nitroalkanes, organic chemistry, oxidation
Abstract:
A synthetic approach to a new class of allyl nitro derivatives is reported. (2-Acetoxy)allyl nitro compounds have been prepared for the first time in a four-step procedure by a preliminary reaction of nitroalkanes with 2-(phenylselenyl)acetaldehyde. After the acetylation of the obtained nitro alcohols, the unsaturation is installed by an oxidation reaction involving the phenylselenyl group followed by a thermal elimination. The oxidation process is accomplished under flow conditions ensuring a notable lowering of overoxidation by products observed in batch.
Agid:
6166646