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Novel regiospecificity in the acid-catalyzed addition of acetic acid to endo-tricyclo[3.2.1.02,4]oct-6-ene

✍ Scribed by M.A. Battiste; J.M. Coxon; R. Edelman

Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
170 KB
Volume
13
Category
Article
ISSN
0040-4039

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✦ Synopsis

We report a striking example of unprecedented regiospecificity in the addition of acetic acid to endo-tricyclo[3.2.1.0z"]oct-6-ene (1). The addition proceeds with surprising ease in acetic acid at 80' (3 days) or at room temperature in the presence of catalytic amounts of toluenesulphonic acid to yield a mixture (22:78) of &-and exo-bicyclo[3.2.l]oct-3-en-2-yl acetates (z! and _2b). The endo-and exo-acetates (2a and 2b)F after hydrolysis to alcohols (3a and 3b),were

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