6533b82efe1ef96bd12945c2
RESEARCH PRODUCT
A study on the aminomercuration-nucleophilic demercuration of --1,5-cyclooctadiene; stereoselective synthesis of 2,6-disubstituted-9-aza bicyclo[3.3.1]nonanes
José BarluengaMiguel A. SalvadóSantiago García-grandaJulia Pérez-prietoGregorio Asensiosubject
chemistry.chemical_classificationReaction mechanismBicyclic molecule15-CyclooctadieneOrganic ChemistryBiochemistrychemistry.chemical_compoundchemistryNucleophileDrug DiscoveryOrganic chemistryAmine gas treatingStereoselectivityCounterionAminationdescription
Abstract The aminomercuration of cis - cis -1,5-Cyclooctadiene with a series of mercury(II) salts followed by nucleophilic displacement of mercury by aromatic amines, water and nitrate ion has been studied. As a result, bicyclic triamines, aminoalcohols and nitrate esters have been obtained respectively in clean processes which occur under total stereoelectronic control by involvement of a tricyclic aziridium ion to afford a single stereoisomer in each case. The influence of the counter ion and the basicity of the amine on the tandem aminomercuration-demercuration is discussed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1992-01-01 | Tetrahedron |