Kinetic study of the substitution reaction of benzyl chloride with triphenylphosphine to synthesize benzyltriphenylphosphonium chloride. Solvent effects

1988 ◽  
Vol 27 (4) ◽  
pp. 555-559 ◽  
Author(s):  
Maw Ling Wang ◽  
Anhong Liu ◽  
Jing Jer Jwo
2021 ◽  
Author(s):  
Umberto Battisti ◽  
Rocío García-Vázquez ◽  
Dennis Svatunek ◽  
Barbara Herrmann ◽  
Andreas Löffler ◽  
...  

Tetrazines (Tz) have been applied as bioorthogonal agents for various biomedical applications including pretargeted imaging approaches. In radioimmunoimaging, pretargeting increases the target-to-background ratio while simultaneously reducing the radiation burden. We have recently reported a strategy to directly 18F-label highly reactive tetrazines based on a 3-(3-fluorophenyl)-Tz core structure. Herein, we report a kinetic study on this versatile scaffold. A library of 40 different tetrazines was prepared, fully characterized, and investigated with emphasis on second order rate constants for the reaction with trans-cyclooctene (TCO). Our results reveal the effects of various substitution patterns and moreover demonstrate the importance of measuring reactivities in the solvent of interest, as click rates in different solvents do not necessarily correlate well. In particular, we report that tetrazines modified in 2-position of the phenyl substituent show high intrinsic reactivity towards TCO, which is diminished in aqueous systems by unfavorable solvent effects. The obtained results enable the prediction of the bioorthogonal reactivity and thereby facilitate the development of the next-generation of substituted aryltetrazines for in vivo application.


Author(s):  
Takumi Oshima ◽  
Kazushi Tamada ◽  
Hatsue Tamura ◽  
Toshikazu Nagai

2015 ◽  
Vol 2 (6) ◽  
pp. 713-720 ◽  
Author(s):  
Akio Kamimura ◽  
Tatsuro Yoshinaga ◽  
Fumiaki Noguchi ◽  
Koichiro Miyazaki ◽  
Hidemitsu Uno

A kinetic study on the intramolecular direct radical substitution reaction on tin atoms was undertaken.


RSC Advances ◽  
2019 ◽  
Vol 9 (43) ◽  
pp. 25177-25183
Author(s):  
Sen-ichi Aizawa ◽  
Kohei Takizawa ◽  
Momoko Aitani

Thorough kinetic study revealed characteristics of the reaction mechanism for arene ruthenium(ii) complexes with bio-related ligands.


2002 ◽  
Vol 232 (1-2) ◽  
pp. 265-276 ◽  
Author(s):  
Paolo Beltrame ◽  
Francesco Demartin ◽  
Giovanni Zuretti

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