Journal of Organic Chemistry p. 839 - 845 (1980)
Update date:2022-08-05
Topics:
Garratt, Dennis G.
Ryan, M. Dominic
Beaulieu, Pierre L.
The reaction of dimethyl endo,endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylate with chlorine, bromine, iodine, benzeneselenenyl chloride, and benzenesulphenyl chloride has been studied.Under conditions of kinetic control both γ- and δ-lactones are formed, the δ lactone being predominant except in the case of bromine.The thermodynamic product distributions favored the δ-lactone exclusively.A general mechanistic scheme is proposed.
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