CORNER BROMINATION OF 2-METHYL-ENDO-TRICYCLO[3.2.1.0(2,4)]OCTANE AND 2-METHYL-ENDO-TRICYCLO[3.2.1.0(2,4)]OCT-6-ENE

Authors
BURRITT A COXON JM STEEL PJ SMITH WB
Citation
A. Burritt et al., CORNER BROMINATION OF 2-METHYL-ENDO-TRICYCLO[3.2.1.0(2,4)]OCTANE AND 2-METHYL-ENDO-TRICYCLO[3.2.1.0(2,4)]OCT-6-ENE, Journal of organic chemistry, 61(11), 1996, pp. 3669-3676
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
11
Year of publication
1996
Pages
3669 - 3676
Database
ISI
SICI code
0022-3263(1996)61:11<3669:CBO2A2>2.0.ZU;2-Y
Abstract
Reaction of 2-methyl-endo-tricyclo[3.2.1.0(2.4)]octane (1) with bromin e in CCl4 gave 2-exo, 3-endodibromo-2-endo-methylbicyclo[3.2.1]octane (3) which rearranges on silica to 2-exo, 6-endo-dibromo-1-methylbicycl o[2.2.2]octane (4). Reaction in methanol gave mo-2-endo-methoxy-2-exo- methylbicyclo[3.2.1]octane (10) and mo-2-endo-methoxy-2-exo-methylbicy clo[3.2.1]octane (11) formed by corner attack of the bromine electroph ile 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 CCl4 and methanol gave products of r eaction at the alkene site.