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Paper | Regular issue | Vol 27, No. 2, 1988, pp.479-494
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4407
Reactions with Cyclic Oxalyl Compounds, Part 26: The Fischer-Indole Rearrangement of Sterically Hindered Systems Part 7: Diaza[n.3.3]propellanes via Thermally Initiated Fischer-Indolization

Gert Kollenz, Ralph Theuer, Walter Ott, Karl Peters, Eva-Maria Peters, and Hans Georg von Schnering

*Max-Planck-Institut für Festkörperforachung , Heisenbergstrasse 1. D-7000 Stuttgart 80, Germany


The 4,5-bridged pyrrol-2,3-diones 3, obtained from cyclocondensation reactions of the N,N-disubstituted hydrazones 2 and oxalyl dichloride, can be rearranged into the corresponding diaza[n.3.3]propellanes 4 via a thermally initiated Fischer - indolization process. Their molecular structure is confirmed with aid of an X-ray structure determination of 4a and chemical degradation reactions leading to the tetracyclic indole systems 5.