Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis and Photoreaction of D-Nor-5α-androstan-16-one Acetylhydrazone in the Presence of Oxygen
Hiroshi SuginomeTsutomu UchidaKazuhiko KizukaTadashi Masamune
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1980 Volume 53 Issue 8 Pages 2285-2291


D-Nor-5α-androstan-16-one was prepared via seven steps from 16-diazo-3β-hydroxyandrost-5-en-17-one. The major products of the photolysis of its acetylhydrazone in dioxane containing oxygen were the parent ketone and 17-oxa-5α-androstan-16-one, accompanied by low yields of three isomeric lactams: 17-aza-5α-androstan-16-one, 16-aza-5α-androstan-17-one, and 17-aza-5α,13α-androstan-16-one. These three are the same lactams formed in the photo-Beckmann rearrangement of the corresponding oxime, D-nor-5α-androstan-16-one oxime. Their formation from the acetylhydrazone may have some mechanistic significance with regard to the path of the formation of lactams in the photolysis of 5α-androstan-17-one acetylhydrazone in the presence of oxygen reported previously. The mass spectrometric fragmentations of fifteen D-nor-5α-androstanes with functional groups at their C-16 positions are described.

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