765-99-1Relevant academic research and scientific papers
Rearrangement and Cleavage of the Grignard Reagent from 5-(Chloromethyl)norbornene
Hill, E. Alexander,Hsieh, King,Condroski, Kevin,Sonnentag, Heidi,Skalitzky, Donald,Gagas, Donald
, p. 5286 - 5292 (2007/10/02)
The Grignard reagents 1-Mg and 2-Mg from endo- and exo-5-(chloromethyl)norbornene rearrange with ring cleavage on heating to yield an allylcyclopentenyl organomagnesium compound (3-Mg).This, in turn, undergoes competitively a variety of reactions, including an alternative cyclization to a bicyclooctene organomagnesium (4-Mg) and formal loss of hydrogen or propene to produce allylcyclopentadienyl- (5-Mg) and cyclopentadienylmagnesium compounds.Endo and exo isomers 1-Mg and 2-Mg rearrange at comparable rates and are partially interconverted, probably via their cleavage and recyclization.Mechanistic possibilities are discussed.
