title: Synthesis of a stable iminium salt and propellane derivatives.
abstract: The treatment of morphinan 1 with NaH and MsCl provided very stable iminium salt 7 possessing propellane skeleton. One of the synthesized iminium salts 7, isobutyl derivative 7b, was crystallized and its structure was determined by X-ray crystallography. The natural bond orbital analysis suggested that the stability of the iminium should result from the stereoelectronic effect (hyperconjugation) attributed to their own structures.
authors.affiliation: School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan. nagaseh@pharm.kitasato-u.ac.jp
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Nagase
authors.forename: Naoshi
authors.initials: N
authors.lastname: Yamamoto
authors.forename: Toru
authors.initials: T
authors.lastname: Nemoto
authors.forename: Kenji
authors.initials: K
authors.lastname: Yoza
authors.forename: Kenshu
authors.initials: K
authors.lastname: Kamiya
authors.forename: Shuichi
authors.initials: S
authors.lastname: Hirono
authors.forename: Shinobu
authors.initials: S
authors.lastname: Momen
authors.forename: Naoki
authors.initials: N
authors.lastname: Izumimoto
authors.forename: Ko
authors.initials: K
authors.lastname: Hasebe
authors.forename: Hidenori
authors.initials: H
authors.lastname: Mochizuki
authors.forename: Hideaki
authors.initials: H
authors.lastname: Fujii
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008698:Mesylates / Q000737:chemistry; D009019:Morphinans / Q000138:chemical synthesis* / Q000737:chemistry; D017670:Sodium Compounds / Q000737:chemistry
chemical_list: D000701:Analgesics, Opioid; D008698:Mesylates; D009019:Morphinans; D017670:Sodium Compounds; C524957:sodium hydride; C030209:methanesulfonyl chloride