Tetrahedron

Transannular π-cyclization in electrophilic additions to 1, 5-dimethylcycloocta-1, 5-diene

G Haufe, A Wolf, K Schulze

文献索引：Haufe, G.; Wolf, A.; Schulze, K. Tetrahedron, 1986 , vol. 42, # 17 p. 4719 - 4728

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被引用次数: 12

摘要

Electrophilic additions of Broensted acids to 1, 5-dimethylcycloocta-1, 5-diene yield syn-8- substituted 1, 5-dimethylbicyclo [3.2. 1] octanes via parallel π-cyclization and subsequent Wagner-Meerwein type rearrangements. The corresponding anti-isomers are synthesized by nucleophilic substitution in the 8-position. The classical or nonclassical structure of the cationic intermediates is discussed.