Journal of Organic Chemistry p. 5286 - 5292 (1989)
Update date:2022-08-03
Topics:
Hill, E. Alexander
Hsieh, King
Condroski, Kevin
Sonnentag, Heidi
Skalitzky, Donald
Gagas, Donald
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 bicyclo<3.3.0>octene 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.
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