Tetrahedron

Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2, 6-diaryl-3, 7-diazatricyclo [4.2. 0.0 2, 5] octan-4, 8-diones induced by LDA

L Di Nunno, P Vitale, A Scilimati

文献索引：Di Nunno, Leonardo; Vitale, Paola; Scilimati, Antonio Tetrahedron, 2008 , vol. 64, # 49 p. 11198 - 11204

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被引用次数: 21

摘要

3-Arylisoxazoles react with LDA in THF at 0° C affording syn-2, 6-diaryl-3, 7-diazatricyclo [4.2. 0.02, 5] octan-4, 8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles ...