- Synthesis of a stable iminium salt and propellane derivatives.
Synthesis of a stable iminium salt and propellane derivatives.
The Journal of organic chemistry (2008-09-25)
Hiroshi Nagase, Naoshi Yamamoto, Toru Nemoto, Kenji Yoza, Kenshu Kamiya, Shuichi Hirono, Shinobu Momen, Naoki Izumimoto, Ko Hasebe, Hidenori Mochizuki, Hideaki Fujii
PMID18811203
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.