Synthesis of a stable iminium salt and propellane derivatives |
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| Authors: | Nagase Hiroshi Yamamoto Naoshi Nemoto Toru Yoza Kenji Kamiya Kenshu Hirono Shuichi Momen Shinobu Izumimoto Naoki Hasebe Ko Mochizuki Hidenori Fujii Hideaki |
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| Affiliation: | School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan. nagaseh@pharm.kitasato-u.ac.jp |
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| 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. |
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