23525-05-5Relevant articles and documents
Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides
Hofstra, Julie L.,Poremba, Kelsey E.,Shimozono, Alex M.,Reisman, Sarah E.
supporting information, p. 14901 - 14905 (2019/11/11)
A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)2?4 H2O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.
STEREOSELECTIVE SYNTHESIS OF CIS-4-METHYLSPHINGOSINE AND DERIVATIVES THEREOF
-
Page/Page column 18-19, (2012/11/14)
The invention provides for synthesis of a (S-R) dihydroxy-amino-methylalkylene characterized by the general formula I, or its R-S diastereomer, wherein R1 is CH2OH or CH2-CH2OH, and R2 is C2 to C20 al
Reactions of cyclohexenyl iodonium tetrafluoroborate with bromide ion: Retardation due to the formation of λ3-bromoiodane
Okuyama, Tadashi,Imamura, Shohei,Fujita, Morifumi
, p. 1609 - 1613 (2007/10/03)
The reaction of 4-tert-butylcyclohex-1-enyl(phenyl)iodonium tetrafluoroborate (1a) and the 4-chlorophenyl derivative (1b) with bromide ion was examined in methanol, acetonitrile, and chloroform. Products include those derived from the intermediate cyclohexenyl cation as well as 1-bromocyclohexene. Kinetic measurements show that the reaction of 1 is strongly retarded by the added bromide. The curved dependence of the observed rate constant on the bromide concentration is typical of a pre-equilibrium formation of the intermediate adduct with a fast bromide-independent reaction (solvolysis of the iodonium ion). The formation of the adduct, λ3-bromoiodane, was also confirmed by the UV spectral change. The relative reactivity of the iodonium ion and λ3-bromoiodane is evaluated to be on the order of 102. The bromide substitution product forms both via the SN1 reaction of the free iodonium ion and via the ligand coupling of the iodane.