Beilstein J. Org. Chem.2013,9, 1781–1790, doi:10.3762/bjoc.9.207
application of a monolithic form of triphenylphosphine to the Ramirezgem-dibromoolefinationreaction using flow chemistry techniques is reported. A variety of gem-dibromides were synthesised in high purity and excellent yield following only removal of solvent and no further off-line purification. It is also
possible to perform the Appel reaction using the same monolith and the relationship between the mechanisms of the two reactions is discussed.
Keywords: bromination; flow chemistry; Ramirezgem-dibromoolefinationreaction; solid-supported reagent; triphenylphosphine monolith; Introduction
The advantages
monolith to the Appel reaction (the transformation of alkyl alcohols to the corresponding bromides), we wished to investigate the application of this monolith to the closely related Ramirezgem-dibromoolefinationreaction; the formation of gem-dibromoolefins from aldehydes or ketones.
In 1962 Ramirez
PDF
Graphical Abstract
Scheme 1:
Formation of gem-dibromoolefin 3 from the reaction of carbon tetrabromide and triphenylphosphine as...