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Synthesis and conformational analysis of phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]- and 1,2,3- oxathiazino[4,3-a]isoquinolines

  • Through the ring closures of tetrahydroisoquinoline 1,3-amino alcohols bearing a phenyl group in the side- chain, diastereomers of novel 1- or 2-phenyl-substituted 1,3,2-oxazaphosphino[4,3-a]isoquinoline 4-oxides, and 1,2,3- oxathiazino[4,3-a]isoquinoline 4-oxides and 4,4-dioxides were prepared. NMR analysis and DFT calculations on the prepared tetrahydroisoquinoline-condensed 1,2,3-heterocycles revealed that their conformational equilibria of cis1-trans-cis2 type are influenced by the relative configuration of P-4 in the 1,3,2-oxazaphosphinanes, and by the position of the phenyl group in the 1,2,3-oxathiazines.

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Contributor(s):Ildikó Schuster, Andreas Koch, Matthias Heydenreich, Erich Kleinpeter, László Lázár, Ferenc Fueloep
Document Type:Article
Year of first Publication:2008
Year of Completion:2008
Release Date:2017/03/24
Source:Journal of Molecular Structure. - 888 (2008), 1-3, S. 124 - 137
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie