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gem-Dimethyl effect in a Grignard reagent cyclization-cleavage rearrangement

EA Hill, DC Link, P Donndelinger

文献索引:Hill, Alexander E.; Link, Daniel C.; Donndelinger Peter Journal of Organic Chemistry, 1981 , vol. 46, # 6 p. 1177 - 1182

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被引用次数: 15

摘要

Summary Detailed analysis of the exchange-broadened'H NMR spectra of 2, 4, 6-t. rihydroxy derivatives of benzaldehyde and acetophenone yield activation enthalpies of 8.0 and 6.9 kcal/mol, respectively, for the exchange of the o-hydroxyl environments. Slightly lower barriers are surmised for the corresponding 2, 6-dihydroxy compounds. Theoretical calculations using approximate molecular orbital theory indicate that the exchange ...