Merck

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
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methanesulfonyl chloride, ≥99.7%
Sigma-Aldrich
Methanesulfonyl chloride, purum, ≥98.0% (AT)