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Combinatorial Chemistry Techniques↗
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Andrew Burritt
Publications and source records attributed to Andrew Burritt.
Bromination of exo-Tricyclo[3.2.2.0(2,4)]non-6-ene.
In carbon tetrachloride reaction of 1 with bromine occurs at the double bond and is favored from the less hindered face, anti to the cyclopropane ring, to give 2 and 3 (2:1) over reaction from the syn face or at the corner of the cyclopropane to give 5. In the solvent methanol, corner attack of bromine at the cycloproane to give 30, 16, 17, and 37 competes with reaction at the double bond anti to the cyclopropane to give 18, 19, and 2.
Journal Article↗
Corner Bromination of 2-Methyl-endo-tricyclo[3.2.1.0(2,4)]octane and -oct-6-ene.
Reaction of 2-methyl-endo-tricyclo[3.2.1.0(2,4)]octane (1) with bromine in CCl(4) gave 2-exo,3-endo-dibromo-2-endo-methylbicyclo[3.2.1]octane (3) which rearranges on silica to 2-exo,6-endo-dibromo-1-methylbicyclo[2.2.2]octane (4). Reaction in methanol gave 4-endo-bromo-2-exo-methoxy-2-endo-methylbicyclo[3.2.1]octane (10) and 4-endo-bromo-2-endo-methoxy-2-exo-methylbicyclo[3.2.1]octane (11) formed by corner attack of the bromine electrophile with C2-C4 bond rupture and inversion of configuration at the site of electrophilic attack. Reaction of 2-methyl-endo-tricyclo[3.2.1.0(2,4)]oct-6-ene (2) with bromine in CCl(4) and methanol gave products of reaction at the alkene site.
Journal Article↗