Synthesis of a Stable Iminium Salt and Propellane Derivatives

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 t...

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Veröffentlicht in:	Journal of organic chemistry 2008-10, Vol.73 (20), p.8093-8096
Hauptverfasser:	Nagase, Hiroshi, Yamamoto, Naoshi, Nemoto, Toru, Yoza, Kenji, Kamiya, Kenshu, Hirono, Shuichi, Momen, Shinobu, Izumimoto, Naoki, Hasebe, Ko, Mochizuki, Hidenori, Fujii, Hideaki
Format:	Artikel
Sprache:	eng
Schlagworte:	Analgesics, Opioid - chemical synthesis Analgesics, Opioid - chemistry Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Mesylates - chemistry Morphinans - chemical synthesis Morphinans - chemistry Organic chemistry Preparations and properties Sodium Compounds - chemistry
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo801276z