R. G. Kostyanovsky, Yu. I. El'natanov, I. I. Chervin, S. V. Konovalikhin, A. B. Zolotoi, L. O. Atovmyan, “Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ<sup>2</sup>-dehydroquinuclidine-2,3-di-carboxylate”, Mendeleev Commun., 1996, Volume 6, Issue 4,Pages <nobr>143

This article is cited in 7 papers

Autoassembling of the quinuclidine nucleus: one-step synthesis, structure and properties of dimethyl 4-hydroxy-6,6,7,7-tetramethyl-Δ²-dehydroquinuclidine-2,3-di-carboxylate

R. G. Kostyanovsky^a, Yu. I. El'natanov^a, I. I. Chervin^a, S. V. Konovalikhin^b, A. B. Zolotoi^b, L. O. Atovmyan^b

^a N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
^b Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

Abstract: Triacetonamine reacts with dimethyl acetylenedicarboxylate in MeOH to give an ordinary adduct, aminomaleate 2, while in aprotic solvents quinuclidine 1 is formed under mild conditions and in high yield; its structure is confirmed by spectroscopic methods as well as X-ray diffraction analysis. A mechanism of autoassembling is proposed, and chemical transformations of 1 with retention of quinuclidine nucleus are studied.

Language: English

DOI: 10.1070/MC1996v006n04ABEH000619