31173-90-7Relevant academic research and scientific papers
Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling
Dupuy, Stéphanie,Zhang, Ke-Feng,Goutierre, Anne-Sophie,Baudoin, Olivier
, p. 14793 - 14797 (2016/11/23)
Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C?H bond functionalization methods. We describe herein a new step-economical approach that enables C?C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
Enantioselective intramolecular benzylic C-H bond amination: Efficient synthesis of optically active benzosultams
Ichinose, Masami,Suematsu, Hidehiro,Yasutomi, Yoichi,Nishioka, Yota,Uchida, Tatsuya,Katsuki, Tsutomu
supporting information; experimental part, p. 9884 - 9887 (2011/12/02)
'Salen' along: The iridium(III)-salen complex 1 efficiently catalyzes the title reaction of 2-ethylbenzenesulfonyl azides to give five-membered sultams with high enantioselectivity. Other 2-alkyl-substitued substrates lead to five- and six-membered sultam
Equilibria of isomeric transformations and relations between thermodynamic properties of secondary alkylbenzenes
Pimerzin, A. A.,Nesterova, T. N.,Rozhnov, A. M.
, p. 641 - 648 (2007/10/02)
Equilibria of mutual transformations of monoamylbenzenes and diamylbenzenes (AmB), monohexylbenzenes (HxB), monoheptylbenzenes (HpB), and monodecylbenzenes (DB) have been studied in the liquid state over the range 273 to 423 K in the presence of 3 to 9 mass per cent of AlCl3.Values of ΔfH0m and ΔfS0m for the reactions studied have been calculated from the temperature dependences of the equilibrium constants.Below are given the reactions and the corresponding values for ΔfH0m/(kJ.mol-1) and ΔfS0m/(J.K-1.mol-1): 3-AmB=2-AmB, -(0.16 +/- 0.08), (8.45 +/- 0.23); 3-HxB=2-HxB, -(0.30 +/- 0.07), (3.85 +/- 0.21); 3-HpB=2-HpB, -(0.21 +/- 0.07), (3.52 +/- 0.22); 3-DB=2-DB, -(0.23 +/- 0.14), (3.51 +/- 0.43); 4-HpB=3-HpB, (0.02 +/- 0.41), (7.57 +/- 1.29); 4-DB=3-DB, (0.09 +/- 0.41), (1.69 +/- 1.28); 5-DB=4-DB, -(0.01 +/- 0.09), (0.18 +/- 0.25).For para-to-meta transformations of diamylbenzenes the average molar reaction enthalpy is -(0.26 +/- 0.46)kJ.mol-1 and the intrinsic change of molar entropy is -(0.99 +/- 1.2)J.K-1.mol-1.It is shown that for the calculation of enthalpies of formation of secondary alkylbenzenes correlations can be used which do not take into account the position of the phenyl substituent on the aliphatic hydrocarbon chain.The calculation of enthalpies of formation of normal and secondary alkylbenzenes in the liquid state at 298.15 K is made on the basis of experimental and literature values.
