76043-69-1Relevant articles and documents
Chromium-carbyne complexes: Intermediates for organic synthesis
Bejot, Romain,He, Anyu,Falck, John R.,Mioskowski, Charles
, p. 1719 - 1722 (2007)
(Chemical Equation Presented) On the same route: Chromium-carbyne complexes are readily prepared by treatment of 1,1,1-trichloromethyl reagents with chromium(II) chloride. They serve as intermediates in the selective formation of a wide variety of products, such as alkynes, alkenes, β-hydroxy ketones, aldehydes, allylic alcohols, and allenes (see scheme, E = electrophile).
An Efficient Route to Aliphatic 2,2-Dichloroaldehydes via Chlorination of Aldehydes or Alcohols with the System Cl2/Quaternary Ammonium Chloride
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco,Pagnoni, Ugo M.,Parsons, Andrew F.,Pinetti, Adriano
, p. 2173 - 2178 (2003)
An effective and low waste method for preparing aliphatic 2,2-dichloroaldehydes has been achieved by halogenation of aldehydes or alcohols with Cl2, using tetraalkylammonium chlorides as recoverable catalysts.
Mechanistically Guided Design of an Efficient and Enantioselective Aminocatalytic α-Chlorination of Aldehydes
Hutchinson, George,Alamillo-Ferrer, Carla,Burés, Jordi
supporting information, p. 6805 - 6809 (2021/05/29)
The enantioselective aminocatalytic α-chlorination of aldehydes is a challenging reaction because of its tendency to proceed through neutral intermediates in unselective pathways. Herein we report the rational shift to a highly selective reaction pathway involving charged intermediates using hexafluoroisopropanol as solvent. This change in mechanism has enabled us to match and improve upon the yields and enantioselectivities displayed by previous methods while using cheaper aminocatalysts and chlorinating agents, 80-95% less amount of catalyst, convenient temperatures, and shorter reaction times.
Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes
Jimeno, Ciril,Cao, Lidong,Renaud, Philippe
, p. 1251 - 1255 (2016/02/19)
Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.