1617-32-9Relevant articles and documents
A Facile Method for the Sulfenyllactonization of Alkenoic Acids Using Dimethyl Sulfoxide Activated by Oxalyl Chloride
Zhang, Ting,Dai, Yifeng,Cheng, Siwei,Liu, Yongguo,Yang, Shaoxiang,Sun, Baoguo,Tian, Hongyu
, p. 1380 - 1386 (2017)
A simple approach has been developed for the sulfenyllactonization of alkenoic acids using dimethyl sulfoxide activated with oxalyl chloride, in which methanesulfenyl chloride is proposed as the intermediate.
THE BARRIER FOR 1,2 HYDROGEN SHIFT IN DIALKYL CARBENES
Stevens, Ian D. R.,Liu, Michael T. H.,Soundararajan, N.,Paike, N.
, p. 481 - 484 (1989)
The products from the thermolysis of 4-diazirinopentanoic acid (2) allow the estimate of an experimental value for the Ea = 1.1 +/- 1 kcal.mol-1 for the barrier height for 1,2 H shift in dialkyl carbenes.
Khasanov et al.
, (1979)
Nickel-catalyzed electrocarboxylation of allylic halides with CO2
Wu, La-Xia,Deng, Fang-Jie,Wu, Lin,Wang, Huan,Chen, Tai-Jie,Guan, Ye-Bin,Lu, Jia-Xing
, p. 13137 - 13141 (2021/08/03)
Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, temperature and additive. β,γ-Unsaturated carboxylic acids were obtained in moderate to good yields and with high chain selectivity. This reaction shows tolerance to functional groups. In addition, cyclic voltammetry was performed to provide the possible mechanism of nickel-catalyzed CO2allylation.
Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes
Am Ende, Christopher W.,Asare-Okai, Papa Nii,Fox, Joseph M.,Jemas, Andrew,O'brien, Jessica G. K.
supporting information, p. 9415 - 9420 (2020/12/21)
Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are much faster than competing mechanisms involving diazo or ylide intermediates. Here, deuterium labeling and diazo compound trapping experiments are employed to demonstrate that both carbene and diazo mechanisms operate in the reactions of a dialkyldiazirine motif that is commonly utilized for biological applications. For the fraction of intermolecular labeling that does involve a carbene mechanism, direct insertion is not necessarily involved, as products derived from a carbonyl ylide are also observed. We demonstrate that a strained cycloalkyne can intercept diazo compound intermediates and serve as a bioorthogonal probe for studying the contribution of the diazonium mechanism of photoaffinity labeling on a model protein under aqueous conditions.