Correction to Withdrawn Article[3,4] Cyclization Products of δ-Oxo-α,β-unsaturated Ketoxime During Reaction with Hydrochloric Acid in Anhydrous Diethyl Ether
✍ Scribed by Cornelia Uncuta; Adriana Tudose; Miron T. Caproiu; Silvia Udrea; Christian Roussel
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 143 KB
- Volume
- 2003
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
We have studied the cyclization of (4__Z__)‐2,2,5,8,8‐pentamethyl‐4‐nonene‐3,7‐dione (3__E__)‐oxime (2). We have previously claimed the formation of a stable 3,5,5‐trisubstituted 3‐isoxazolidinol and of a bridged bicycle 4,5‐dihydro‐2,5‐methano‐1,4,3‐dioxazepine in the reaction of 2 with hydrochloric acid in anhydrous diethyl ether. We report in this article that the above compounds are actually 3,3‐dimethyl‐1‐(5′‐tert‐butyl‐5′‐hydroxy‐3′‐methylisoxazolidin‐3′‐yl)butan‐2‐one (5) and 1,3‐di‐tert‐butyl‐5‐methyl‐2,7‐dioxa‐6‐azabicyclo[3.2.1]oct‐3‐ene (6). The formation of these products involves the splitting of hydroxylamine in 2 and its re‐addition as an O‐nucleophile under acidic reaction conditions. Surprisingly, 5 provided the 2‐isoxazoline derivative 3 on heating or on standing in CDCl~3~/TFA solution at room temperature. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)