title: Rearrangement of a mesylate tropane intermediate in nucleophilic substitution reactions. Synthesis of aza-bicyclo[3.2.1]octane and aza-bicyclo[3.2.2]nonane ethers, imides, and amines.
abstract: Nucleophilic substitution of 2beta-mesyloxymethyl-N-methyl-3beta-p-tolyl-tropane intermediate with alkoxides, metal imides, or amines was found to lead not only to the expected bicyclo[3.2.1]octane (tropane) ether, imide, and amine derivatives but also to unexpected bicyclo[3.2.2]nonane derivatives. When alkoxides were used as nucleophile, only the rearranged bicyclo[3.2.2]nonane structure was obtained, whereas the use of amines or imides as nucleophile afforded a mixture of the two structures. The bicyclo[3.2.2]nonane structure was assigned by NMR analysis.
authors.affiliation: Department of Psychiatry, Yale University and VA CT HCS, West Haven, Connecticut, USA.
authors.forename: Lionel
authors.initials: L
authors.lastname: Ogier
authors.forename: Frédéric
authors.initials: F
authors.lastname: Turpin
authors.forename: Ronald M
authors.initials: RM
authors.lastname: Baldwin
authors.forename: Françoise
authors.initials: F
authors.lastname: Riché
authors.forename: Ho
authors.initials: H
authors.lastname: Law
authors.forename: Robert B
authors.initials: RB
authors.lastname: Innis
authors.forename: Gilles
authors.initials: G
authors.lastname: Tamagnan
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis; D000588:Amines / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis*; D007094:Imides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008698:Mesylates / Q000737:chemistry; D009795:Octanes / Q000138:chemical synthesis; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000473:Alkanes; D000588:Amines; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D004987:Ethers; D007094:Imides; D008698:Mesylates; D009795:Octanes; D014326:Tropanes; C017573:nonane