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Silacyclohexanes and silaheterocyclohexanes-why are they so different from other heterocyclohexanes?

  • Stereochemical studies on silaheterocyclohexanes is a 'hot topic' as evidenced by the growing number of publications. During last 10 years a substantial number of substituted silacyclohexanes and heterocyclohexanes containing sulfur, oxygen or nitrogen as the second (or third) heteroatom have been synthesized and studied by variable temperature dynamic NMR spectroscopy, gas-phase electron diffraction, variable temperature IR, Raman, microwave spectroscopy with respect to thermodynamic (frozen conformational equilibria) and kinetic (barrier to ring inversion) information. As the stereochemistry of cyclohexane and its N-, O-, P-, S-hetero analogues is one of keystones of modern theoretical and synthetic organic and heterocyclic chemistry, the stereochemistry of silacyclohexane and its hetero analogs is an important element of theoretical and synthetic organosilicon chemistry. The various classes of saturated six-membered rings were critically compared and studied in detail with respect to differences in their stereochemistry and dynamicStereochemical studies on silaheterocyclohexanes is a 'hot topic' as evidenced by the growing number of publications. During last 10 years a substantial number of substituted silacyclohexanes and heterocyclohexanes containing sulfur, oxygen or nitrogen as the second (or third) heteroatom have been synthesized and studied by variable temperature dynamic NMR spectroscopy, gas-phase electron diffraction, variable temperature IR, Raman, microwave spectroscopy with respect to thermodynamic (frozen conformational equilibria) and kinetic (barrier to ring inversion) information. As the stereochemistry of cyclohexane and its N-, O-, P-, S-hetero analogues is one of keystones of modern theoretical and synthetic organic and heterocyclic chemistry, the stereochemistry of silacyclohexane and its hetero analogs is an important element of theoretical and synthetic organosilicon chemistry. The various classes of saturated six-membered rings were critically compared and studied in detail with respect to differences in their stereochemistry and dynamic behavior.show moreshow less

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Metadaten
Author:Bagrat A. Shainyan, Erich Kleinpeter
DOI:https://doi.org/10.1016/j.tet.2013.04.126
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:Barrier to ring inversion; Conformational equilibrium; Electrostatic effects; Silacyclohexanes; Silaheterocyclohexanes; Steric effects
Volume:69
Issue:29
Pagenumber:10
First Page:5927
Last Page:5936
Funder:Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [RFBR-DFG 08-03-91954, 11-03-91334]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert