Synthesis of New Phosphonoamide and Phosphonocaprolactam Derivatives via the Diethyl Chlorophosphate-Promoted Beckmann Rearrangement of γ-Phosphonyloximes

Aymen Wahbi

Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021 Jarzouna, Tunisia

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Soufiane Touil,

Corresponding Author

Soufiane Touil

Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021 Jarzouna, Tunisia

Correspondence to: Soufiane Touil; e-mail: [email protected].Search for more papers by this author

Aymen Wahbi,

Aymen Wahbi

Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021 Jarzouna, Tunisia

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Soufiane Touil,

Corresponding Author

Soufiane Touil

Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte, University of Carthage, 7021 Jarzouna, Tunisia

Correspondence to: Soufiane Touil; e-mail: [email protected].Search for more papers by this author

First published: 23 June 2015

https://doi.org/10.1002/hc.21273

Citations: 9

Contract grant sponsor: Tunisian Ministry of Higher Education and Scientific Research.

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ABSTRACT

Herein, we report an efficient and straightforward synthesis of new phosphonoamide and phosphonocaprolactam derivatives, via the Beckmann rearrangement of γ-phosphonyloximes. The reaction proceeded smoothly in the presence of diethyl chlorophosphate as a promoter, to afford the title compounds in satisfactory yields. A mechanistic rationalization for this reaction is provided allowing for the prediction of its regiochemistry.

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Synthesis of New Phosphonoamide and Phosphonocaprolactam Derivatives via the Diethyl Chlorophosphate-Promoted Beckmann Rearrangement of γ-Phosphonyloximes

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Synthesis of New Phosphonoamide and Phosphonocaprolactam Derivatives via the Diethyl Chlorophosphate-Promoted Beckmann Rearrangement of γ-Phosphonyloximes

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