58443-86-0Relevant articles and documents
An electron-catalyzed cope cyclization. The structure of the 2,5-dicyano-1,5-hexadiene radical anion in the gas phase
Hammad, Loubna A.,Wenthold, Paul G.
, p. 10796 - 10797 (2003)
The radical anion of 2,5-dicyano-1,5-hexadiene is shown to undergo Cope cyclization in a flowing afterglow-triple quadrupole apparatus. The cyclic structure of the 2,5-dicyano-1,5-hexadiene radical anion was established by using chemical reactivity. The i
Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations
Dong, Xichang,Roeckl, Johannes L.,Waldvogel, Siegfried R.,Morandi, Bill
, (2021/02/12)
Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.
En route to stable all-carbon-substituted silylenes: Synthesis and reactivity of a bis(α-spirocyclopropyl)silylene
Redies, Kai M.,Fallon, Thomas,Oestreich, Martin
supporting information, p. 3235 - 3238 (2014/08/05)
The synthesis of a bis(α-spirocyclopropyl)silylene is reported and its reactivity revealed. Liberation of the silylene was accomplished by UV-light-mediated photolysis of a trisilane precursor. Insertion and addition reactions prove the existence and versatility of this new family of bis(α-spirocyclopropyl)-substituted silylenes. Substitution on the flanking cyclopropyls for improved steric shielding of the reactive center remains challenging.
Removal of water - a factor influencing the synthesis of alkynes in a phase-transfer catalyzed β-elimination reaction
Zakrzewski,Huras,Sas,Zelechowski,Bombinska
, p. 1051 - 1057 (2008/09/21)
Acetylene derivatives 4 were synthesized from the corresponding vicinal bromo compounds 2 in the phase-transfer catalyzed hydrogen bromide β-elimination reaction using solid potassium hydroxide as a base, xylene as a solvent, and a phase-transfer catalyst. The yields of the synthesized acetylene derivatives 4 were substantially improved when water formed in the process had been removed.
Enantioselective total synthesis of (+)-testudinariol A using a new nickel-catalyzed allenyl aldehyde cyclization
Amarasinghe, Kande K. D.,Montgomery, John
, p. 9366 - 9367 (2007/10/03)
An enantioselective total synthesis of (+)-testudinariol A was completed. A new nickel-catalyzed allenyl aldehyde cyclization was developed in the approach. In addition, an asymmetric anti aldol reaction and a two-directional oxocarbenium ion/vinyl silane condensation were employed as key steps. Copyright