18240-70-5Relevant articles and documents
Total synthesis of (+)- and (-)-decursivine and (±)-serotobenine through a cascade witkop photocyclization/elimination/addition sequence: Scope and mechanistic insights
Hu, Weimin,Qin, Hua,Cui, Yuxin,Jia, Yanxing
supporting information, p. 3139 - 3147 (2013/03/28)
In this article, the total syntheses of antimalarial compound decursivine and its biologically inactive sibling serotobenine are presented. The biomimetic synthesis of (±)-serotobenine was investigated first, but failed. During the subsequent investigatio
2,2-dichloroaldehydes and 2,2-dichlorocarboxylic acids from 2- picoline·HCl catalyzed chlorination of aldehydes
Bellesia, Franco,De Buyck, Laurent,Ghelfi, Franco
, p. 146 - 148 (2007/10/03)
An efficient preparation of 2,2-dichloroaldehydes and 2,2- dichlorocarboxylic acids has been achieved by chlorination of aldehydes using 2-picoline hydrochloride as recoverable catalyst.
α,α-DICHLOROALDEHYDES AND α,α-DICHLOROCARBOXYLIC ACIDS FROM LONG CHAIN 1-ALKANOLS. IMPROVED CHLORINATION IN THE SYSTEM DMF-CHCl3-MgCl2
Buyck, L. De,Casaert, F.,Lepeleire, C. De,Schamp, N.
, p. 525 - 534 (2007/10/02)
Production of α,α-dichloroaldehydes by direct chlorination of 1-alkanols with chlorine gas, catalyzed by DMF and DMF*HCl, was extended to long chain compounds (CnH2n+1OH; n = 5, 6, 8, 10, 12, 14, 16, 18).Two problems specific to the longer chains were solved to obtain isolated yields in the range 70-85 percent; a) parasitic radical chlorination was largely controlled by shielding from light; b) alkyl alkanoate side product (8 percent for n = 8 but 25 percent for n = 16 or 18) was decreased to 0-2 percent in the presence of MgCl2*H2O.Homogeneity of the reaction medium was improved with chloroform as a cosolvent.Oxidation of the aldehydes to dichlorocarboxylic acids proceeded smoothly with aqueous KMnO4 up to the tetradecanal.For the longer chains 30 percent hydrogen peroxide-NaHCO3 in acetone (overnight at 48-52 deg C) was the preferred oxidant.