Corner attack on exo-and endo-tricyclo [3.2. 1.02, 4] octane by deuteron and mercuric ions

JM Coxon, PJ Steel, BI Whittington…

文献索引：Coxon, James M.; Steel, Peter J.; Whittington, Barry I.; Battiste, Merle A. Journal of Organic Chemistry, 1989 , vol. 54, # 6 p. 1383 - 1391

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被引用次数: 26

摘要

Reaction of endo-tricyclo [3.2. 1.02~ 4] octane (1) with deuteron in methanol-dl gave a mixture (62: 38) of methoxy ethers 3b and 4b from cleavage of the most substituted cyclopropane bond. The reaction proceeds by attack of deuterium at the corner of the cyclopropane. Trapping of the intermediate cation 5b is competitive with rearrangement to the nonclassical cation 6b. Reaction of exo-tricycle [3.2. 1.02 v4] octane (2) under similar ...