C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy

Larina, Lyudmila

doi:10.3390/ijms24119646

Open AccessReview

C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy

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Lyudmila Larina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., 664033 Irkutsk, Russia

Int. J. Mol. Sci. 2023, 24(11), 9646; https://doi.org/10.3390/ijms24119646

Submission received: 13 April 2023 / Revised: 25 May 2023 / Accepted: 28 May 2023 / Published: 1 June 2023

(This article belongs to the Special Issue NMR Spectroscopy in Materials Chemistry)

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Abstract

The review presents extensive data (from the works of the author and literature) on the structure of C- and N-chlorophosphorylated enamines and the related heterocycles obtained by multipulse multinuclear ¹H, ¹³C, and ³¹P NMR spectroscopy. The use of phosphorus pentachloride as a phosphorylating agent for functional enamines enables the synthesis of various C- and N-phosphorylated products that are heterocyclized to form various promising nitrogen- and phosphorus-containing heterocyclic systems. ³¹P NMR spectroscopy is the most convenient, reliable and unambiguous method for the study and identification of organophosphorus compounds with different coordination numbers of the phosphorus atom, as well as for the determination of their Z- and E-isomeric forms. An alteration of the coordination number of the phosphorus atom in the phosphorylated compounds from 3 to 6 leads to a drastic screening of the ³¹P nucleus from about +200 to −300 ppm. The unique structural features of nitrogen–phosphorus-containing heterocyclic compounds are discussed.

Keywords: C- and N-chlorophosphorylated enamines; nitrogen–phosphorus-containing heterocycles; phosphorus pentachloride; E- and Z-isomers; structure; 2D and ¹H, ¹³C and ³¹P NMR spectroscopy; ³⁵Cl NQR spectroscopy

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Larina, L. C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy. Int. J. Mol. Sci. 2023, 24, 9646. https://doi.org/10.3390/ijms24119646

AMA Style

Larina L. C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy. International Journal of Molecular Sciences. 2023; 24(11):9646. https://doi.org/10.3390/ijms24119646

Chicago/Turabian Style

Larina, Lyudmila. 2023. "C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy" International Journal of Molecular Sciences 24, no. 11: 9646. https://doi.org/10.3390/ijms24119646

APA Style

Larina, L. (2023). C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy. International Journal of Molecular Sciences, 24(11), 9646. https://doi.org/10.3390/ijms24119646

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C- and N-Phosphorylated Enamines—An Avenue to Heterocycles: NMR Spectroscopy

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