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Report | Regular issue | Vol 22, No. 4, 1984, pp.803-806
Published online, 1st January, 1970
DOI: 10.3987/R-1984-04-0803
Reduction of the Herbicide Diquat with Sodium Borohydridenickel (II) Chloride: Structure of the Two Isomeric Perhydro-8a,10a-diazaphenanthrenes

Shigeo Ukai,* Shozo Kawase, Susumu Kanno, Tadashi Kiho, Masaru Kido, and Iwao Miura

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

The stereochemistry of isomeric perhydro-8a,10a-diazaphenanthrenes(2 and 3) obtained by sodium borohydride-nickel (II) chloride reduction of the herbicide, diquat (1), was confirmed by X-ray crystallographic analysis of the hydrobromide of 2, and of the hydrochloride of partially reduced product, 1,4,4a,4b,5,8,9,10-octahydxo-8a,10a-diazaphenanthrene(6), which is converted with ease to 3.