Ungewöhnliche Reaktivität gespannter Brückenkopfderivate | Zendy

Martínez Antonio García | Zendy; Fraile Amelia García | Zendy

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Ungewöhnliche Reaktivität gespannter Brückenkopfderivate

Author(s) -

Martínez Antonio García,

Fraile Amelia García

Publication year - 1983

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19831161025

Subject(s) - chemistry , 2 norbornyl cation , norbornane , steric effects , solvolysis , epimer , reactivity (psychology) , medicinal chemistry , stereochemistry , organic chemistry , hydrolysis , medicine , alternative medicine , pathology

Unusual Reactivity of Strained Bridgehead Derivatives The solvolysis of 7,7‐dimethyl‐1, exo ‐2‐bis(trifluoromethylsulfonyloxy)norbornane ( 5 ) in Et 2 O/I 2 Mg and 80% MeOH proceeds with formation of substituted 2‐norbornyl cations, yielding 1, exo ‐2‐diiodo‐7,7‐dimethylnorbornane ( 9 ) and camphenilone ( 13 ), respectively. When the vic ‐diiodide 9 is treated with LiAlH 4 /C 6 H 6 partial epimerization to 1, endo ‐2‐diiodo‐7,7‐dimethylnorbornane ( 12 ) is observed without reduction; this result is probably due to steric hindrance of the reactants.

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