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Benign Chlorine-Free Approaches to Organophosphorus Compounds

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Chemistry Beyond Chlorine

Abstract

Organophosphorus compounds have widespread use throughout the world, as agricultural chemicals, medicinal agents, flame retardants, plasticizing and stabilizing agents, selective extractants for metal salts from ores, additives for petroleum products and corrosion inhibitors. Moreover, they are also endowed with metal binding properties, for this reason they have a paramount role in catalysis, being able to direct the activity and selectivity of a metal. Currently, organophosphorus compounds are produced on industrial scale using white phosphorus and chlorine, through an environmentally harmful process which generates equimolar amount of chlorinated waste. In the quest for alternative environmentally benign technology, several routes have been envisaged starting either from elemental phosphorus or from one of its direct low-valent derivative as hypophosphite.

In this contribution, we summarize the latest findings on “green” synthetic approaches towards organophosphorus derivatives. Reactions of elemental phosphorus with organic molecules by means of photochemical irradiation, through a radical mechanism, by electrophilic/nucleophilic addition, mediated by a transition metal or by electrochemical means, will be described. Moreover, a synthetic strategy that uses hypophosphorus acid and its alkali salts as phosphorylating agents towards organic molecules will be as well depicted.

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Acknowledgements

Thanks are expressed to the EC project SUSPHOS, RFP7-PEOPLE-2012-ITN - 317404 “A European Training Network for Sus tainable Phos phorus Chemistry” for funding this research activity and to ECRF project Firenze Hydrolab-2 for a grant to MSR.

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  1. Istituto di Chimica dei Composti Organometallici – Consiglio Nazionale delle Ricerche (ICCOM – CNR), Via Madonna del Piano, 10, 50019, Sesto Fiorentino (FI), Italy

    Maria Caporali, Manuel Serrano-Ruiz & Maurizio Peruzzini

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  1. Maria Caporali
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  2. Manuel Serrano-Ruiz
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  3. Maurizio Peruzzini
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Correspondence to Maurizio Peruzzini .

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Editors and Affiliations

  1. Ca' Foscari University of Venice Environmental Sciences, Venice, Italy

    Pietro Tundo

  2. Institute of Elemento-Organic Chemistry, Nankai University Institute of Elemento-Organic Chemistry, Tianjin, China

    Liang-Nian He

  3. Chemistry Department, Lomonosov Moscow State University Chemistry Department, Moscow, Russia

    Ekaterina Lokteva

  4. Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro-RJ, Brazil

    Claudio Mota

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Caporali, M., Serrano-Ruiz, M., Peruzzini, M. (2016). Benign Chlorine-Free Approaches to Organophosphorus Compounds. In: Tundo, P., He, LN., Lokteva, E., Mota, C. (eds) Chemistry Beyond Chlorine. Springer, Cham. https://doi.org/10.1007/978-3-319-30073-3_3

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