The title compound, 2-{2-[1,3-di-tert-butyl-4-(tert-butyl-amino)-2-(tert-butyl-imino)-1,3,2λ(5),4-diaza-diphosphetidin-2-yl]-1-(4-meth-oxy-phen-yl)prop-2-en-1-yl}-5,5-dimethyl-1,3,2λ(5)-dioxaphosphinan-2-one, C(31)H(57)N(4)O(4)P(3), was synthesized from the Phospha-Michael addition reaction of cyclo-diphos-pha-zane [(t-BuNH)P(μ-Nt-Bu)](2) and allenyl-phospho-nate [(OCH(2)C(CH(3))(2)CH(2)O)P(O)C(p-CH(3)O-C(6)H(4))=C=CH(2)]. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules. The structure exhibits pseudosymmetry but attempts to solve it in a higher (monoclinic) space group were unsuccessful.
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http://dx.doi.org/10.1107/S1600536811014127 | DOI Listing |
The addition of phosphines (PR) to Michael acceptors is a key step in many Lewis-base catalysed reactions. The kinetics of the reactions of ten phosphines with ethyl acrylate, ethyl allenoate, ethyl propiolate, ethenesulfonyl fluoride, and ethyl 2-butynoate in dichloromethane at 20 °C was followed by photometric and NMR spectroscopic methods. The experimentally determined second-order rate constants show that electronic effects in sterically unencumbered phosphines affect their nucleophilicity towards different classes of Michael acceptors in the same ordering.
View Article and Find Full Text PDFOrg Biomol Chem
November 2023
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, 2025 Chengluo Avenue, Chengdu 610016, P. R. China.
A Hg(OTf)-catalyzed tandem -Michael addition/cyclization/dehydration of 2-hydroxychalcones with -phosphine oxides is presented. This protocol provides a new and supplementary approach for the preparation of 4-phosphorylated 4-chromenes in good yields (up to 99%). In addition, this domino reaction allows the successful construction of two new C-P and C-O bonds in a one-pot operation.
View Article and Find Full Text PDFPolymers (Basel)
July 2023
Fraunhofer Institute for Structural Durability and System Reliability LBF, 64289 Darmstadt, Germany.
The increasing demand to provide sustainably produced plastic materials requires, a.o., the development of biobased flame retardants (FRs) for applications where flame retardancy is essential.
View Article and Find Full Text PDFChemistry
May 2023
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1-5/10, 8093, Zürich, Switzerland.
A N-hydroxy succinimide (NHS) ester substituted bis(acyl)phosphane oxide (ACTIVE-BAPO) was prepared by phospha-Michael addition and used for an easy one-step BAPO ligation with substrates containing primary amino groups, such as amino acids, proteins, and poly(amidoamine) (PAMAM) dendrimers. Thereby, a range of new molecular and polymeric photoinitators was obtained. Real-time photo-rheology experiments demonstrated the outstanding efficiency of the PAMAM BAPOs as photoinitiators for free radical polymerization.
View Article and Find Full Text PDFMolecules
November 2022
Key Laboratory of Molecular Enzymology and Engineering of Ministry of Education, School of Life Sciences, Jilin University, Changchun 130023, China.
Organophosphorus compounds are the core structure of many active natural products. The synthesis of these compounds is generally achieved by metal catalysis requiring specifically functionalized substrates or harsh conditions. Herein, we disclose the phospha-Michael addition reaction of biphenyphosphine oxide with various substituted β-nitrostyrenes or benzylidene malononitriles.
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