Acid-catalyzed hydration of 5-substituted norbornenes

Lejunen, Martti

doi:10.1021/ar00116a005

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1986

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Cited by 7 publications

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Protolytische Spaltung von Tricyclo[3.2.0.0 ^2,7 ]hept‐3‐en

Kirmse

Streu

1988

Chem. Ber.

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Protolytk Cleavage of Tricyclo[32.O.@'Ibept-3eneAcidolyscs of the title compound 9 were performed in aqueous dioxane and in acetic acid to give eight alcohols (5-8,lO-13) among which bicyclo[3.1 .I]hept-2-en-exo-6-01 (13) was novel.Comparison with independent routes to the various cationic intermediates reveals that the double bond and the cyclopropane ring of 9 react at similar rates and with high regioselectivity. Protonation occurs preferentially, if not exclusively, at C-4 and C-7. 551 -553 (1988)

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