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The stereochemistry of bicyclo[3.2.1]octane—XVIII

Identifieur interne : 003864 ( Istex/Curation ); précédent : 003863; suivant : 003865

The stereochemistry of bicyclo[3.2.1]octane—XVIII

Auteurs : C. W. Jefford [États-Unis] ; W. Wojnarowski [États-Unis]

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RBID : ISTEX:EE26D1DA649D60DCB95B95A8141174B4ABCBE217

English descriptors

Abstract

Abstract: Monochlorocarbene undergoes addition to bicyclo[2.2.2]octene-2 to give anti- and syn-3-chlorotricyclo[3.2.2.02,4]nonane in a ratio of 5:1. On warming the mixture, only the syn isomer rearranges to 2-chlorobicyclo[3.2.2]nonene-3. The addition of monochlorocarbene to 1-methylnorbomene-2 affords 1-methyl-anti-3-chloro-exo-tricyclo[3.2.1.02,4]octane. 1-methyl-exo-4-chlorobicyclo[3.2.1]octene-2 and 1-methyl-exo-2-chlorobicyclo[3.2.1]octene-3 in a ratio of 3:1:1. Similar addition to 2-methylnorbomene-2 gives 2-methyl-anti-3-chloro-exo-tricyclo[3.2.1.02,4]octane and 2-methylenebicyclo[3.2.1]octene-3 in a ratio of 10:1. The exo-anti tricyclic structures are stable to heat and aqueous silver ion. In contrast, the exo-syn adducts are remarkably labile and are assumed to be the precursors of the rearranged products. The factors which govern the stereochemistry of the addition and rearrangement processes are discussed.

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DOI: 10.1016/S0040-4020(01)82760-5

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ISTEX:EE26D1DA649D60DCB95B95A8141174B4ABCBE217

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<div type="abstract" xml:lang="en">Abstract: Monochlorocarbene undergoes addition to bicyclo[2.2.2]octene-2 to give anti- and syn-3-chlorotricyclo[3.2.2.02,4]nonane in a ratio of 5:1. On warming the mixture, only the syn isomer rearranges to 2-chlorobicyclo[3.2.2]nonene-3. The addition of monochlorocarbene to 1-methylnorbomene-2 affords 1-methyl-anti-3-chloro-exo-tricyclo[3.2.1.02,4]octane. 1-methyl-exo-4-chlorobicyclo[3.2.1]octene-2 and 1-methyl-exo-2-chlorobicyclo[3.2.1]octene-3 in a ratio of 3:1:1. Similar addition to 2-methylnorbomene-2 gives 2-methyl-anti-3-chloro-exo-tricyclo[3.2.1.02,4]octane and 2-methylenebicyclo[3.2.1]octene-3 in a ratio of 10:1. The exo-anti tricyclic structures are stable to heat and aqueous silver ion. In contrast, the exo-syn adducts are remarkably labile and are assumed to be the precursors of the rearranged products. The factors which govern the stereochemistry of the addition and rearrangement processes are discussed.</div>
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