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Gabrielli S, Mariotti N, Chiurchiù E, et al. Synthetic Approach to the Preparation of (2-Acetoxy)allyl Nitro Compounds. J Org Chem. 2018;83(20):12855-12862doi: 10.1021/acs.joc.8b01744.
Gabrielli, S., Mariotti, N., Chiurchiù, E., Ballini, R., Petrini, M., & Palmieri, A. (2018). Synthetic Approach to the Preparation of (2-Acetoxy)allyl Nitro Compounds. The Journal of organic chemistry, 83(20), 12855-12862. https://doi.org/10.1021/acs.joc.8b01744
Gabrielli, Serena, et al. "Synthetic Approach to the Preparation of (2-Acetoxy)allyl Nitro Compounds." The Journal of organic chemistry vol. 83,20 (2018): 12855-12862. doi: https://doi.org/10.1021/acs.joc.8b01744
Gabrielli S, Mariotti N, Chiurchiù E, Ballini R, Petrini M, Palmieri A. Synthetic Approach to the Preparation of (2-Acetoxy)allyl Nitro Compounds. J Org Chem. 2018 Oct 19;83(20):12855-12862. doi: 10.1021/acs.joc.8b01744. Epub 2018 Oct 08. PMID: 30251854.
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J Org Chem. 2018 Oct 19;83(20):12855-12862. doi: 10.1021/acs.joc.8b01744. Epub 2018 Oct 08.

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

The Journal of organic chemistry

Serena Gabrielli, Nicole Mariotti, Elena Chiurchiù, Roberto Ballini, Marino Petrini, Alessandro Palmieri

Affiliations

  1. Green Chemistry Group, School of Science and Technology, Chemistry Division , University of Camerino , Via S. Agostino 1 , Camerino , Macerata 62032 , Italy.

PMID: 30251854 DOI: 10.1021/acs.joc.8b01744

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.

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