Synthetic studies on the lythraceae alkaloids-IX1 1 Other papers in this series: I.J. Quick and R. Oterson, Tetrahedron Letters 745 (1977); II, Ref. 8a; III, Ref. 8b; IV, Ref. 3a; V, Ref. 14; VI, Ref. 12; VII, Ref. 18; VIII, Ref. 13. Vanadium (V) oxidation of some seco-alkaloids

Article abstract of DOI:10.1016/0040-4020(80)85040-X

Seco-alkaloids 4-7 were treated with VOF₃ and VOCl₃, under a variety of conditions. No coupled products were detected. However, ring chlorinated and side-chain oxidized products were obtained from the VOCl₃ oxidation of 4 and 7 respectively. The generality of the ring chlorination reaction was confirmed by chlorination of simple 0-methoxy phenols under these conditions to yield 17 and 23. In certain cases, 21 and 22, intermolecular coupling occurs in preference to chlorination.