caa a22 4500 469038039 CHVBK 20180323132801.0 cr unu---uuuuu 170328e19921201xx s 000 0 eng 10.1007/BF00808282 doi (NATIONALLICENCE)springer-10.1007/BF00808282 Regiospecific synthesis and structural study of some trifluoromethyl substituted dibenzosemibullvalenes [Elektronische Daten] [Klaudio Otočan, Mladen Mintas, Fritz Kastner, Albrecht Mannschreck, James Golen, Paul Williard] Regiospezifische Synthese und Strukturuntersuchung einiger Trifluormethyl-substituierter Dibenzosemibullvalene Summary: Preparation of the regiospecifically trifluoromethyl substituted dibenzosemibullvalenes3 and5 is described. An unequivocal proof of chirality of3 and5 was obtained by enrichment of their enantiomers using liquid chromatography on triacetyl- or tribenzoylcellulose. The stereostructure of compounds3 to5 was proved by their1H-NMR spectra and confirmed by X-ray crystallographic analysis. The geometrical data from X-ray structural analyses showed that five-membered rings involved in the skeleton of3 and5 adopt flattened envelope conformations. These results indicate also a significant substituent-induced bond length asymmetry in the cyclopropane rings of3 and5. Springer-Verlag, 1992 Dibenzobarrelene nationallicence Dibenzosemibullvalene nationallicence Enantioselective chromatography nationallicence Trifluoromethylation nationallicence Photochemical rearrangement nationallicence X-ray crystal structures nationallicence Otočan Klaudio Department of Organic Chemistry, University of Zagreb, 4100, Zagreb, Croatia aut Mintas Mladen Department of Organic Chemistry, University of Zagreb, 4100, Zagreb, Croatia aut Kastner Fritz Institute of Organic Chemistry, University of Regensburg, D-W-8400, Regensburg, Federal Republic of Germany aut Mannschreck Albrecht Institute of Organic Chemistry, University of Regensburg, D-W-8400, Regensburg, Federal Republic of Germany aut Golen James Department of Chemistry, Brown University, 02912, Providence, Rhode Island, USA aut Williard Paul Department of Chemistry, Brown University, 02912, Providence, Rhode Island, USA aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/12(1992-12-01), 1193-1205 0026-9247 123:12<1193 1992 123 706 https://doi.org/10.1007/BF00808282 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00808282 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Otočan Klaudio Department of Organic Chemistry, University of Zagreb, 4100, Zagreb, Croatia aut NATIONALLICENCE 700 1- Mintas Mladen Department of Organic Chemistry, University of Zagreb, 4100, Zagreb, Croatia aut NATIONALLICENCE 700 1- Kastner Fritz Institute of Organic Chemistry, University of Regensburg, D-W-8400, Regensburg, Federal Republic of Germany aut NATIONALLICENCE 700 1- Mannschreck Albrecht Institute of Organic Chemistry, University of Regensburg, D-W-8400, Regensburg, Federal Republic of Germany aut NATIONALLICENCE 700 1- Golen James Department of Chemistry, Brown University, 02912, Providence, Rhode Island, USA aut NATIONALLICENCE 700 1- Williard Paul Department of Chemistry, Brown University, 02912, Providence, Rhode Island, USA aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/12(1992-12-01), 1193-1205 0026-9247 123:12<1193 1992 123 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer