Issue 73, 2023

Stannyl phosphaketene as a synthon for phosphorus analogues of β-lactams

Abstract

The reaction of the stannyl phosphaketene (Nacnac)SnPCO 1 (Nacnac = CH{(CMe)(2,6-iPr2C6H3N)}2) with B(C6F5)3 produced the 1,4-addition product of (Nacnac)SnPCO(B(C6F5)3). However, the corresponding reactions in the presence of dimethyl maleate, diisopropyl fumarate or diethyl-but-2-ynedioate gave [2+2] addition yielding four-membered phosphacycles, ((Nacnac)Sn(MeO2C))CHPC(OB(C6F5)3)CH(CO2Me), [(C6F5)3B)PC(OSn)C(CO2Me)CH(CO2Me)]2, (Nacnac)Sn(iPrO2C)CC(OAl(C6F5)3)P[CH(CO2iPr)CH2(CO2iPr)]CH(CO2iPr), and (Nacnac)SnP (EtO2CCC(CO2Et))CO(B(C6F5)3), respectively. In contrast, the corresponding reaction of phenylacetylene gave the FLP-addition product (Nacnac)SnOC(P)C(Ph)CH(B(C6F5)3). Collectively, this reactivity demonstrates that the stannyl phosphaketene 1 can act as a synthon for P-analogues of β-lactam derivatives.

Graphical abstract: Stannyl phosphaketene as a synthon for phosphorus analogues of β-lactams

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
28 Jun 2023
Accepted
15 Aug 2023
First published
15 Aug 2023

Chem. Commun., 2023,59, 10956-10959

Stannyl phosphaketene as a synthon for phosphorus analogues of β-lactams

Y. Luo, Z. Zhao, T. Chen, Y. Li, Y. Zhao, D. W. Stephan and Y. Wu, Chem. Commun., 2023, 59, 10956 DOI: 10.1039/D3CC03117A

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