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2005
Bridged compounds
Q 0060
Amides Containing Two Norbornene Fragments. Synthesis and Chemical Trans— Reaction of the diastereomerically pure aminomethylnorbornenes (I)
18- 069 formation.
and (VI) with diastereomerically pure norbornenylcarbonyl chlorides (II) and (IX) provides access to the four possible stereopure amides containing two norbornene fragments, e.g. (III), (VII) and (X). Epoxidation of only one of the two double bonds is impossible as demonstrated by H2O2 oxidation [cf. (IV), (VIII) and (XI)] as well as by
calculation of the activation energies. Oxidation of the amides with endo-orientation of
the carbonyl group, e.g. (X), provides a heterocyclization by-product (XII). —
(KAS'YAN, L. I.; ISAEV, A. K.; KAS'YAN, A. O.; GOLODAEVA, E. A.;
KARPENKO, D. V.; TARABARA, I. N.; Russ. J. Org. Chem. 40 (2004) 10,
1415-1426; Dep. Org. Chem., Dnepropetrovsk Natl. Univ., Dnepropetrovsk 49050,
Ukraine; Eng.) — Mischke
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