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Acid-catalyzed rearrangement of some steroidal isoxazolidines

✍ Scribed by Milica M. Rajković; L.jubinka B. Lorenc; Ivan O. Juranić; Željko J. Vitnik; Mihailo Lj. Mihailovic

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
588 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Acid-catalyzed reaction of the steroidal A~-unsaturated 313,513-epoxyimino compound 2 and A3-unsaturated 113,513epoxyimino products 3 and 7, results in intramolecular rearrangement involving the N-CH 3 group to give the corresponding perhydro-3,1-oxazine derivatives 9-11. Under similar reaction conditions, the saturated analogues 4, 6 and 8 remain unchanged. The difference in reactivity between the unsaturated and saturated compounds is studied and elucidated by the semiempirical molecular orbital MNDO-PM3 method.

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