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Article

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

by
Jakub Adamek
1,2,*,
Anna Węgrzyk-Schlieter
1,2,
Klaudia Steć
1,2,
Krzysztof Walczak
1 and
Karol Erfurt
3
1
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland
2
Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland
3
Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(18), 3405; https://doi.org/10.3390/molecules24183405
Submission received: 9 September 2019 / Revised: 15 September 2019 / Accepted: 16 September 2019 / Published: 19 September 2019
(This article belongs to the Special Issue Recent Developments in the Synthesis and Utilization of Organophosphorus Compounds)
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Abstract

In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.
Keywords: organophosphorus chemistry; phosphonium salts; phosphonates; phosphinates; phosphine oxides organophosphorus chemistry; phosphonium salts; phosphonates; phosphinates; phosphine oxides
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MDPI and ACS Style

Adamek, J.; Węgrzyk-Schlieter, A.; Steć, K.; Walczak, K.; Erfurt, K. Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles. Molecules 2019, 24, 3405. https://doi.org/10.3390/molecules24183405

AMA Style

Adamek J, Węgrzyk-Schlieter A, Steć K, Walczak K, Erfurt K. Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles. Molecules. 2019; 24(18):3405. https://doi.org/10.3390/molecules24183405

Chicago/Turabian Style

Adamek, Jakub, Anna Węgrzyk-Schlieter, Klaudia Steć, Krzysztof Walczak, and Karol Erfurt. 2019. "Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles" Molecules 24, no. 18: 3405. https://doi.org/10.3390/molecules24183405

APA Style

Adamek, J., Węgrzyk-Schlieter, A., Steć, K., Walczak, K., & Erfurt, K. (2019). Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles. Molecules, 24(18), 3405. https://doi.org/10.3390/molecules24183405

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