Configuration and Conformation Study of S-Allyl O-Methyl N-(2- and 4-Substituted Acridin-9-yl)thiocarbonimidates in Relation to Their [3,3] Sigmatropic Rearrangement

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Title:Configuration and Conformation Study of S-Allyl O-Methyl N-(2- and 4-Substituted Acridin-9-yl)thiocarbonimidates in Relation to Their [3,3] Sigmatropic Rearrangement
Creators:
Danihel, Ivan
Pihlaja, Kalevi
Imrich, Ján
Suchár, Gejza
Kristian, Pavol
Böhm, Stanislav
Hočová, Slávka
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 3, pp. 387-393
Uncontrolled Keywords:PM3 and HF/3-21G calculations, NOE NMR spectroscopy, Dipole moments, Acridines, Thiocarbonimidates

Abstract

Configuration and conformations of <i>S</i>-allyl <i>O</i>-methyl <i>N</i>-(2- and 4-substituted acridin-9-yl)thiocarbonimidates were studied by means of NMR spectroscopy, dipole moments and quantum chemical calculations. The <i>E</i> configuration was proved for the unsubstituted and 2-chloro derivatives from the NOE-difference spectra. Experimental values of dipole moments were related to those obtained from vector addition. Quantum chemical calculations pointed to the chair conformation of these compounds in transition state for above-mentioned rearrangement.

Title:Configuration and Conformation Study of S-Allyl O-Methyl N-(2- and 4-Substituted Acridin-9-yl)thiocarbonimidates in Relation to Their [3,3] Sigmatropic Rearrangement
Creators:
Danihel, Ivan
Pihlaja, Kalevi
Imrich, Ján
Suchár, Gejza
Kristian, Pavol
Böhm, Stanislav
Hočová, Slávka
Uncontrolled Keywords:PM3 and HF/3-21G calculations, NOE NMR spectroscopy, Dipole moments, Acridines, Thiocarbonimidates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:3
Page Range:pp. 387-393
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980387UNSPECIFIED
ID Code:1306
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Danihel, Ivan; Pihlaja, Kalevi; Imrich, Ján; Suchár, Gejza; Kristian, Pavol; Böhm, Stanislav; Hočová, Slávka (1998) Configuration and Conformation Study of S-Allyl O-Methyl N-(2- and 4-Substituted Acridin-9-yl)thiocarbonimidates in Relation to Their [3,3] Sigmatropic Rearrangement. Collection of Czechoslovak Chemical Communications, 63 (3). pp. 387-393. ISSN 0010-0765

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