Indene dimerization products

Abstract

The reaction of 1H-indene (indene) in the presence of Friedel-Crafts acids was studied. As expected [M. Spiteller, J. Jovanovic, Fuel 78(1999)1263] there were dimers and trimers in the product mixture together with higher oligomers. Among products with double molecular weight relative to the molecular weight of indene, the structure of four compounds was determined: 6-(2?,3?-dihydro-1?H-inden-1?-yl)-1H-indene 2-(2?,3?-dihydro-1?H-inden-1?-yl)-1H-indene 1-(2?,3?-dihydro-1?H-inden-2?-yl)-1H-indene and 2,3,1?,3?-tetrahydro-[1,2?]biindenylidene. It was shown that the first one represents an indene alkylation product and that the others were obtained by bonding of the indan-1-ylium ion and indene at the position 2, followed by acid catalyzed 1,2-hydride rearrangement in the case of the third and fourth one. Considering the indene dimerization products as components of pyrolysis oils and as interesting compounds to be used as model substances for NMR, MS and X-ray analysis, the reaction, separation and isolation parameters were optimized in this study.

Diels–Alder Reaction of Biofuran Derivatives and Cycloolefin for Directional Synthesis of Fused Ring Hydrocarbon High Density Jet Fuel

“…The side reaction is the polymerization of IND with MFIN and dimerization of IND. 42 The Diels−Alder reaction of 2-MF and IND is similar to that of 2-MF and NBE. The blank reaction of 2-MF with IND is carried out at 190 °C for 7 h without a catalyst, and there are no products generated.…”

“…Methyl perhydrofluorene with a density of more than 0.96 g/mL and a freezing point of less than −20 °C can be obtained by the hydrodeoxygenation of MFIN, which means that MFIN is an excellent high energy density fuel precursor. The side reaction is the polymerization of IND with MFIN and dimerization of IND …”

2,3,1′,3′-Tetrahydro-[1,2′]biindenylidene

“…The compound obtained was, however, spiro [1,1a,6,6atetrahydrocyclopropa[a]indene-1,1 H -2 H ,3 H -dihydro-1 H H-indene] (Jovanovic et al, 2002b). We have now succeeded in isolating (I) from a reaction mixture obtained by treating 1H-indene with H 2 SO 4 (Jovanovic et al, 2002) and in determining its crystal structure. The formula of the reaction product given in the literature by Bell & Spanswick (1966) is incorrect.…”

Chemical and carbon isotopic evolution of hydrocarbons during prograde metamorphism from 100°C to 550°C: Case study in the Liassic black shale formation of Central Swiss Alps

“…The distributions of the aromatic compounds in metamorphic samples show a similar pattern characterized by the predominance of bibenzyl (I), 1-methyl-2-[(3-methylphenyl)methyl]benzene (IV), 1-methyl-3-[(4-methylphenyl)methyl]benzene (V), cadalene (VI) and 2,3-dihydro-1,1,3-trimethyl-3-phenyl 1H-indene (VII). Bibenzyl (I), derivate products of indene, ethylene naphthalene and hydrogenated aromatic hydrocarbons are observed in hydrous pyrolysis products from coal and oil (e.g., Spiteller and Jovanović, 1999;Jovanović et al, 2002;Nuzzi and Marcandalli, 2003). The cadalene-type sesquiterpenoids (compounds III and VI) are associated with a terrestrial plant origin (Albaiges et al, 1984) and are thought to be formed by reductive processes, probably by decarboxylation of the resin fatty acid precursors linked to the kerogen (Otto and Simoneit, 2002) with concurrent hydrogenation and oxidation leading to the aromatic counterparts (cadalene; VI).…”