Anomalous 5-endo-trig reversals: general reactions of 7-oxabicyclo [2.2. 1] heptenes and heptanes

BA Keay, D Rajapaksa…

文献索引：Keay, B. A.; Rajapaksa, D; Rodrigo, R. Canadian Journal of Chemistry, 1984 , vol. 62, p. 1093 - 1098

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被引用次数: 29

摘要

Two general 5-endo-trig reversals of 7-oxabicyclo [2.2. 1] heptanes and heptenes are described and discussed. The reverse-Michael reaction occurs with the aldehyde, ketone, ester, and nitrile derivatives while the reverse aldol reaction catalysed by acid is confined to the aldehydes and ketones. These properties of the title compounds are rationalized in terms of the geometric alignments of the bonding and antibonding orbitals of the bridging ...