68940-37-4Relevant academic research and scientific papers
ELEKTRONENREICHE HEPTAFULVENE: OXIDATIVE DIMERISIERUNG ZU BI-2,4,6-CYCLOHEPTATRIEN-1-YL-VERBINDUNGEN
Bauer, Walter,Daub, Joerg,Hasenhuendl, Adelheid,Rapp, Knut M.,Schmidt, Peter
, p. 2977 - 2980 (1981)
Oxidation reactions of 8,8'-bis-(dimethylamino)-heptafulvene (1c) and lithium-8-dimethylamino-heptafulvene-8-olate (1d) with iodine are described.Spectroscopic data of the new compounds are given.
Charge Separation on Molecular Basis: Chemoselectivity, Regio-, and Stereoselectivity of C-C Bond Formation as Probes for Electron-Transfer Processes
Aurbach, Irmgard,Ponti, Pier Paolo,Salbeck, Erika,Schmuck, Heike,Daub, Joerg
, p. 1101 - 1108 (2007/10/02)
Lithium 8-(dimethylamino)heptafulven-8-olate (1), containing the cross-conjugated heptafulvene structural unit, was investigated with respect to SET (single-electron transfer)-type and polar mechanisms in reactions with methyl iodide and with the carbonyl compounds benzaldehyde (2a), benzophenone (2b), methyl phenylglyoxylate (2c), benzil (2d), and 4-nitrobenzaldehyde (2e).The selectivity of product formation was used as a mechanistic probe.Experimentally, two reaction pathways with different chemoselectivity were observed: Oxidative dimerisation of the heptafulvene 1 accompanied by reduction of the carbonyl compound and "aldol-type" reactions.The specific outcome depends on the electronic properties of the carbonyl compounds.A qualitative correlation between the reduction potentials of the carbonyl compounds and the products formed has been found.
Cross Conjugated Enolates: Structure Characterization of Two Lithium Heptafulvenolates
Bauer, Walter,Daub, Joerg,Rapp, Knut M.
, p. 1777 - 1786 (2007/10/02)
When deprotonated, N,N-dimethylcycloheptatriene-7-carboxamide (2a) and cycloheptatriene-7-carboxylic acid (2c) yield the amide anion 4a and the acid dianion 4c.Due to the NMR spectra, 4a and c have heptafulvene structure with the lithium bound to oxygen.The electron spectra of 4a and c show in the range of 600 - 700 nm three and two signals, respectively.The spectra are temperature and solvent dependent.The THF-solution of 4c is paramagnetic.The structures of the organolithium compounds are discussed.
