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Gas-phase acid-induced ring opening in diastereoisomeric 9,10-oxides derived from trans-1,2,3,4,4a,10a-hexahydrophenanthrene

✍ Scribed by Patrizio Cecchi; Marco Chini; Paolo Crotti; Adriano Pizzabiocca; Gabriele Renzi; Maurizio Speranza

Publisher: Elsevier Science
Year: 1991
Tongue: French
Weight: 629 KB
Volume: 47
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86474-7

No coin nor oath required. For personal study only.

✦ Synopsis

The stereochemical outcome of the two diastereoisomeric rigid benzocondensed epoxides 2a and 2b in the acid-induced nucleophilic attack by MeOH in the gas-phase was studied and compared with the corresponding results obtained with the mobile epoxides of type I. The stereochemistry of the ring opening process in these systems (I, 2a, 6) appears to be dependent on the extent of the positive charge developed at the benzylic carbon. A rationalization which implies different benzylic carbocationic species is proposed, while the hypothesis of the intermediacy offully developed benzylic carbenium ions does not appear to

be supported by the present results.

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