Unknown

Dataset Information

0

1-Imidoalkylphosphonium salts with modulated C?-P+ bond strength: synthesis and application as new active ?-imidoalkylating agents.

ABSTRACT: An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative ?-methoxylation of N-phthaloyl- or N-succinylamino acids to the corresponding N-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties of the obtained 1-imidoalkylphosphonium salts were tested using the Tscherniac-Einhorn-type reaction with aromatic hydrocarbons as a model reaction. It was found that the C?-P+ bond strength can be considerably reduced and the imidoalkylation of arenes can be markedly facilitated using 1-imidoalkylphosphonium salts derived from triarylphosphines with electron-withdrawing substituents such as tris(m-chorophenyl)phosphine, tris(p-chlorophenyl)phosphine and tris[p-(trifluoromethyl)phenyl]phosphine. Microwave irradiation also considerably facilitates the cleavage of the highly polar C?-P+ bond.

SUBMITTER: Adamek J 

PROVIDER: S-EPMC5550811 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

1-Imidoalkylphosphonium salts with modulated C<sub>α</sub>-P<sup>+</sup> bond strength: synthesis and application as new active α-imidoalkylating agents.

Adamek Jakub J   Mazurkiewicz Roman R   Węgrzyk Anna A   Erfurt Karol K  

Beilstein journal of organic chemistry 20170724

An effective synthesis of the hitherto unknown 1-imidoalkylphosphonium salts has been developed in the reported study. The crucial step in the method included the decarboxylative α-methoxylation of <i>N</i>-phthaloyl- or <i>N</i>-succinylamino acids to the corresponding <i>N</i>-(1-methoxyalkyl)imides, followed by the displacement of the methoxy group by the triarylphosphonium group through melting of the imide derivative with triarylphosphonium tetrafluoroborate. The imidoalkylating properties  ...[more]

Similar Datasets

Unknown 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P⁺ Bond Strength-Synthetic Applications.
| S-EPMC6222910 | biostudies-literature
Unknown Unraveling the Potential of Vitamin B<sub>3</sub>-Derived Salts with a Salicylate Anion as Dermal Active Agents for Acne Treatment.
| S-EPMC11372839 | biostudies-literature
Unknown Efficient and Inexpensive Synthesis of <sup>15</sup>N-Labeled 2-Azido-1,3-dimethylimidazolinium Salts Using Na<sup>15</sup>NO<sub>2</sub> Instead of Na<sup>15</sup>NNN.
| S-EPMC10870284 | biostudies-literature
Unknown Solid-Phase Peptide Modification via Deaminative Photochemical Csp<sup>3</sup> -Csp<sup>3</sup> Bond Formation Using Katritzky Salts.
| S-EPMC9401037 | biostudies-literature
Unknown Sunlight active U<sub>3</sub>O<sub>8</sub>@ZnO nanocomposite superfast photocatalyst: synthesis, characterization and application.
| S-EPMC9473160 | biostudies-literature
Unknown Unsaturated Vinyl-Type Carbocation [(CH<sub>3</sub>)<sub>2</sub>C=CH]<sup>+</sup> in Its Carborane Salts.
| S-EPMC8223440 | biostudies-literature
Unknown AIEgens for dark through-bond energy transfer: design, synthesis, theoretical study and application in ratiometric Hg<sup>2+</sup> sensing.
| S-EPMC5398306 | biostudies-literature
Unknown The ionic salts with super oxidizing ions O<sub>2</sub> <sup>+</sup> and N<sub>5</sub> <sup>+</sup>: Potential candidates for high-energy oxidants.
| S-EPMC9532705 | biostudies-literature
Unknown Synthesis and Characterization of Ir-(κ<sup>2</sup>-NSi) Species Active toward the Solventless Hydrolysis of HSiMe(OSiMe<sub>3</sub>)<sub>2</sub>.
| S-EPMC10468103 | biostudies-literature
Unknown Isolable fluorinated triphenylmethyl cation salts of [HCB<sub>11</sub>Cl<sub>11</sub>]<sup>-</sup>: demonstration of remarkable hydride affinity.
| S-EPMC9067617 | biostudies-literature