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Communication | Special issue | Vol 39, No. 2, 1994, pp.485-490
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)73
Steric Requirements and High Pressure Influence on the Thermal Deoxygenation of N-Oxides of Orellanine-like Structure

Róza Antkowiak, Wieslaw Z. Antkowiak,* Izabela Banczyk, Grzegorz Czerwinski, Janusz Jurczak, Jerzy Raczko, and Piotr Salanski

*Facluty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznán, Poland

Abstract

5-Hydroxy-9,10-dihydro-4-azaphenanthrene-N-oxide (1) and its methyl ether (2) were found to undergo the facile thermally induced N-oxide oxygen elimination characteristic for the orellanine-like structures. The relationship between the conformation of the N-oxides, the functional group being part of an oximinopropenoxy system, and the deoxygenation temperature requirements is discussed. The significant decrease of the deoxygenation temperature caused by the pressure of 12 kbar in the case of 2 is supposed to indicate the concerted character of the transformation.