L. Yu. Ukhin, L. G. Kuz'mina, T. N. Gribanova, L. V. Belousova, E. N. Shepelenko, G. S. Borodkin, O. I. Dmitrieva, V. A. Podshibyakin, N. V. Stankevich, “An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives”, Mendeleev Commun., 2021, Volume 31, Issue 2,Pages <nobr>251

Communications

An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives

L. Yu. Ukhin^a, L. G. Kuz'mina^b, T. N. Gribanova^a, L. V. Belousova^a, E. N. Shepelenko^c, G. S. Borodkin^a, O. I. Dmitrieva^a, V. A. Podshibyakin^a, N. V. Stankevich^a

^a Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
^b N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
^c Southern Scientific Center of the Russian Academy of Sciences, Rostov-on-Don, Russian Federation

Abstract: N-Methylation of cotarnine–phenol propargyl ethers conjugates with MeI affords the corresponding quaternary ammonium derivatives with retained acetylenic moiety. 3-Hydroxyalk-1-yn-1-yl analogues in the course of such iodomethylation undergo isomerization into allenic derivatives which are transformed into acetylenic ones upon dissolution in DMSO.

Keywords: cotarnine acetylene derivatives, isoquinolinium compounds, iodomethylation, acetylene–allene rearrangement, X-ray, quantum-chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2021.03.036

	*Supplementary materials:*
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