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

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

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Citation Number: 21

Abstract

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 ...