Tetrahedron Letters p. 2389 - 2392 (1994)
Update date:2022-08-05
Topics:
Warrener, Ronald N.
Maksimovic, Ljiljana
The endo,endo-2,3-dibromo-7-oxanorborneno<2,3-c>succinimide (1) undergoes complete inversion upon hydrogenolysis of the bromine substituents to form (5) (Zn/Ag couple in THF) or (26) (H2, Pd/C).The highly reactive dienophile, N-methyl 7-oxanorbornadieno<2,3-c>maleimide (3) is shown to be a transient intermediates in the Zn/Ag couple experiments by trapping with furan.Deuterium labelling experiments have been used to help elucidate the mechanism of these reactions.
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