1194-95-2Relevant academic research and scientific papers
Aliphatic C-H activation with aluminium trichloride-acetyl chloride: Expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons
Lyall, Catherine L.,Uosis-Martin, Mario,Lowe, John P.,Mahon, Mary F.,Panto?, G. Dan,Lewis, Simon E.
supporting information, p. 1468 - 1475 (2013/05/21)
The functionalisation of decalin by means of an "aliphatic Friedel-Crafts" reaction was reported over fifty years ago by Baddeley et al. This protocol is of current relevance in the context of C-H activation and here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation of the products is described and a mechanistic rationale for their formation is presented. The "aliphatic Friedel-Crafts" procedure allows for production of novel oxygenated building blocks from abundant hydrocarbons and as such can be considered to add significant synthetic value in a single step.
Singlet and Triplet Excited-state Formation in High-energy Electron Tracks in Liquid cis- and trans-Decalin as studied by Product Formation in Radiolysis and Photolysis
Hummel, A.,Leng, H. C. de,Luthjens, L. H.,Wojnarovits, L.
, p. 2459 - 2466 (2007/10/02)
The yields of products formed as a result of irradiation of liquid cis- and trans-decalin with γ-rays and 3 MeV electrons as well as with 7.6 eV photons have been determined by means of gas-liquid chromatography (GLC).The major products for both cis- and trans-decalin are hydrogen, unsaturated C10 products and dimers; in the case of cis-decalin, cis-trans isomerization takes place via a chain reaction.Singlet and triplet excited states are formed by direct excitation and by charge recombination in the tracks of high-energy electrons.The product formation resulting from the singlets is determined by the photolysis.From a knowledge of the total yield of singlets from the radiolysis, the contribution of the singlet excited states to product formation during radiolysis is calculated and the remaining products are assigned to the triplets.For the sum of the yields of singlets and triplets a value of 6.4 (100 eV)-1 (=6.6E-7 mol J-1) is found for cis-decalin and 6.0 (100 eV)-1 (=6.2E-7 mol J-1) for trans-decalin and for the singlet fractions 0.53 and 0.47 in cis- and trans-decalin, respectively.The probability of C-H bond breakage in the singlet and triplet states is 0.42 and 0.82, respectively, for cis-decalin and 0.50 and 0.94, respectively, for trans-decalin.
Composition of Mixtures of Hydrocarbons after BIRCH-Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Carbohexa-1,4-dienes
Beger, J.,Thomas, B.,Vogel, T.,Kirmse, K.,Lang, R.
, p. 481 - 488 (2007/10/02)
10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2.The product mixture compositions are determined through capillary GLC.On storage at +6 deg C some rearomatization of the 1,4-cyclohexadienes 2 occurs.Data of the 1H- and 13C-.n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given.For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized.Acid-catalyzed addition of alcohols to the 1,4-cyclohexadienes systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30percent.Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.
STEREOSELECTIVE FORMATION OF A HYDRINDANE RING SYSTEM BY ANIONIC OLEFIN CYCLIZATION. TRAPPING OF THE ALKYLLITHIUM INTERMEDIATE WITH ELECTROPHILES.
Chamberlin, Richard A.,Bloom, Steven H.
, p. 551 - 554 (2007/10/02)
Cyclopentane formation via the intramolecular addition of a cyclic vinyllithium reagent to a simple alkenes produces a single hydrindane alkyllithium diastereomer that can be trapped with electrophiles.
