R. G. Kostyanovsky, Yu. I. El'natanov, I. I. Chervin, S. V. Konovalikhin, L. O. Atovmyan, A. Rauk, “Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ<sup>2</sup>-dehydro-quinuclidine-2,3-dicarboxylic acid esters”, Mendeleev Commun., 1996, Volume 6, Issue 3,Pages <nobr>108

This article is cited in 2 papers

Heterolytic fragmentation of 4-hydroxy-6,6,7,7-tetramethyl-Δ²-dehydro-quinuclidine-2,3-dicarboxylic acid esters

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

^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
^c Department of Chemistry, University of Calgary, Calgary, Alberta, Canada

Abstract: The title quinuclidines undergo cleavage under the action of acids or H₂O to give Δ²-dehydro-4-piperidones 4, 5 and isobutylene; the resulting redistribution of bond lengths upon N-protonation has been demonstated by X-ray diffraction methods for picrate 2a as well as by ab initio calculations for quinuclidine la, cation 2a’ and zwitterion 2a”, the latter being the most suitable as an intermediate of the fragmentation.

Language: English

DOI: 10.1070/MC1996v006n03ABEH000602