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• W2103453491 abstract "Die Ketone 1-Indanon (6a) und seine Derivate 6b, c und e lasen sich durch niedrigewertiges Titansalz (TiCl4/Zn in THF) zu den entsprechenden Olefinen kuppeln (1a/2a 92:8, 1b/2b 88:12, 1c, e). Die analoge Kupplung von 1-Tetralon (12a) ergibt die Olefine 3a und 4a (ca. 7:3); aus 12b entsteht 3b. Die entsprechende Kupplung der Fluorenone 13 gelingt auch zum an C-1 bzw. C-8 unsubstituierten 5b. – Die bevorzugten Konformation der Olefine 1 – 5 werden mittels Kraftfeld-Rechnungen (Allinger's MMPI) diskutiert; sie erweisen sich, durch die Torsion und out-of-plane-Deformation der zentralen Doppelbindung verursacht, als chiral. Die Konformationen der Olefine 2b und 3b sind aufgrund der 1H-NMR-Spektren stabil, in allen anderen Fällen erfolgt bei Raumtemperatur leichte Racemisierung. Für 3a, b und 12c wird unter den möglichen Konformationen ausschließlich die “twist-boat”-Form als stabil gefunden. Der Einfluß von Methyl-bzw. tert-Butylgruppen an C-1 und C-8 auf die Geometrien der Fluorenylidenfluorene 5c, d und e wird berechnet. Reductive Coupling Reactions of Ketones of the Type of 1-Indanone, 1-Tetralone, and 9-Fluorenone; Conformational Effects in the Series of Indanylidenindanes and Tetralinylidenetetralins1) The ketones 1-indanone (6a) and its derivatives 6b, c and e are coupled by low-valent titanium salts (TiCl4/Zn in THF) to form the corresponding olefins (1a/2a 92:8, 1b/2b 88:12, 1c,e). Reductive coupling of 1-tetralone (12a) yields the olefins 3a and 4a (ca. 7:3); from 12b only 3b is isolated. The analogous coupling of the fluorenones 13 can also be achieved with 13b, which is not substituted at C-1 and C-8. – The preferred conformations of olefins 1 – 5 are discussed using force-field calculations (Allinger's MMPI); as a result of torsion and out-of-plane deformations of the central double bond these systems are found to be chiral. According to the 1H NMR spectra olefins 2b and 3b have a stable configuration, in all other cases fast racemization is observed at room temperature. For olefins 3a, b and 12c a “twist-boat” structure is calculated as the only stable form among the possible conformations. The influence of methyl and tert-butyl groups at C-1 and C-8 on the geometries of fluorenylidenefluorenes 5c, d, and e is investigated." @default.
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• W2103453491 title "Reduktive Kupplungsreaktionen von Ketonen aus der Reihe des 1‐Indanons, 1‐Tetralons und 9‐Fluorenons; konformative Effekete in der Reihe der Indanylidenindane und Tetralinylidentetraline" @default.
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• W2103453491 doi "https://doi.org/10.1002/cber.19841170703" @default.
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