1267779-26-9Relevant academic research and scientific papers
The Chloroazaphosphatrane Motif for Halogen Bonding in Solution
Li, Chunyang,Manick, Anne-Doriane,Yang, Jian,Givaudan, David,Biletskyi, Bohdan,Michaud-Chevalier, Sabine,Dutasta, Jean-Pierre,Hérault, Damien,Bugaut, Xavier,Chatelet, Bastien,Martinez, Alexandre
, p. 11964 - 11973 (2021)
Chloroazaphosphatranes, the corresponding halogenophosphonium cations of the Verkade superbases, were evaluated as a new motif for halogen bonding (XB). Their modulable synthesis allowed for synthetizing chloroazaphosphatranes with various substituents on the nitrogen atoms. The binding constants determined from NMR titration experiments for Cl-, Br-, I-, AcO-, and CN- anions are comparable to those obtained with conventional iodine-based monodentate XB receptors. Remarkably, the protonated azaphosphatrane counterparts display no affinity for anions under the same conditions. The strength of the XB interaction is, to some extent, related to the basicity of the corresponding Verkade superbase. The halogen bonding abilities of this new class of halogen donor motif were also revealed by the Δδ(31P) NMR shift observed in CD2Cl2 solution in the presence of triethylphosphine oxide (TEPO). Thus, chloroazaphosphatranes constitute a new class of halogen bond donors, expanding the repertory of XB motifs mainly based on CAr-I bonds.
Verkade's Superbase as an Organocatalyst for the Strecker Reaction
Yang, Jian,Chatelet, Bastien,Ziarelli, Fabio,Dufaud, Véronique,Hérault, Damien,Martinez, Alexandre
supporting information, p. 6328 - 6332 (2018/11/23)
Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low
Encaging the Verkade's superbases: Thermodynamic and kinetic consequences
Raytchev, Pascal Dimitrov,Martinez, Alexandre,Gornitzka, Heinz,Dutasta, Jean-Pierre
, p. 2157 - 2159 (2011/04/23)
Proazaphosphatranes, also known as Verkade's superbases, are nonionic species, which exhibit catalytic properties for a wide range of reactions. The properly designed host molecule 3 and its protonated counterpart [3·H]+Cl- were synthesized to study how confinement can modify the stability and the reactivity of a Verkade's superbase. The results show that the encapsulation does not alter the strong basicity of the proazaphosphatrane, but dramatically decreases the rate of proton transfer.
