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Mustard Carbonate Analogues: Influence of the Leaving Group on the Neighboring Effect

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Department of Environmental Science, Informatics and Statistics, Ca’ Foscari University of Venice, Campus Scientifico, Via Torino 155, 30170 Venezia Mestre, Italy
Cite this: ACS Sustainable Chem. Eng. 2016, 4, 5, 2843–2851
Publication Date (Web):April 8, 2016
https://doi.org/10.1021/acssuschemeng.6b00425
Copyright © 2016 American Chemical Society

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    Abstract

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    The substitution of a chlorine atom with a carbonate moiety in mustard compounds has led to a new class of molecules, namely, mustard carbonates that retain the reactivity of the well-know toxic iprites but are safe for the operator and the environment. In this paper, for the first time, the influence of the leaving group on the anchimeric effect of sulfur mustard carbonates has been investigated both in autoclave and neat conditions. Results have led to an enhanced selectivity of the anchimerically driven alkylation, as well as to improved and more accessible reaction conditions.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.6b00425.

    • 1H NMR, 13C NMR spectra, GC-MS analysis, and HPLC analysis of the new isolated pure products. (PDF)

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    Cited By

    This article is cited by 7 publications.

    1. Esther Gómez-Caballero, Roberto Martínez-Álvarez, Miguel A. Sierra. Unexpected Reaction Pathways Leading to Thiodiglycol During the Degradation of Long-Chain Sulfur Mustards. The Journal of Organic Chemistry 2018, 83 (20) , 12432-12439. https://doi.org/10.1021/acs.joc.8b01670
    2. Pietro Tundo, Fabio Aricò. Reaction Pathways in Carbonates and Esters. ChemSusChem 2023, 16 (23) https://doi.org/10.1002/cssc.202300748
    3. Monica Viviano, Giacomo Trapasso, Mattia Annatelli, Ciro Milite, Sabrina Castellano, Fabio Aricò. Microwave-Assisted Aminoalkylation of Phenols via Mustard Carbonate Analogues. Synthesis 2022, 54 (11) , 2595-2603. https://doi.org/10.1055/a-1742-3723
    4. Giacomo Trapasso, Claudio Salaris, Marco Reich, Evgenia Logunova, Cristiano Salata, Klaus Kümmerer, Alberto Figoli, Fabio Aricò. A scale-up procedure to dialkyl carbonates; evaluation of their properties, biodegradability, and toxicity. Sustainable Chemistry and Pharmacy 2022, 26 , 100639. https://doi.org/10.1016/j.scp.2022.100639
    5. Mattia Annatelli, Giacomo Trapasso, Claudio Salaris, Cristiano Salata, Sabrina Castellano, Fabio Aricò. Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols. European Journal of Organic Chemistry 2021, 2021 (24) , 3459-3464. https://doi.org/10.1002/ejoc.202100328
    6. Pietro Tundo, Manuele Musolino, Fabio Aricò. Dialkyl Carbonates in the Green Synthesis of Heterocycles. Frontiers in Chemistry 2019, 7 https://doi.org/10.3389/fchem.2019.00300
    7. P. Tundo, M. Musolino, F. Aricò. The reactions of dimethyl carbonate and its derivatives. Green Chemistry 2018, 20 (1) , 28-85. https://doi.org/10.1039/C7GC01764B

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