83164-95-8Relevant academic research and scientific papers
Generation of arynes using trimethylsilylmethyl Grignard reagent for activation of ortho-Iodoaryl or ortho-sulfinylaryl triflates
Yoshida, Suguru,Uchida, Keisuke,Hosoya, Takamitsu
supporting information, p. 691 - 693 (2015/05/27)
The trimethylsilylmethyl Grignard reagent triggered efficient generation of arynes from various ortho-iodoaryl or ortho-sulfinylaryl triflates. The moderate nucleophilicity and basicity of the reagent facilitated efficient reactions between the aryne prec
Generation of arynes via ate complexes of arylboronic esters with an ortho-leaving group
Sumida, Yuto,Kato, Tomoe,Hosoya, Takamitsu
supporting information, p. 2806 - 2809 (2013/07/11)
An efficient method of generating aryne has been achieved by treating ortho-(trifluoromethanesulfonyloxy)arylboronic acid pinacol ester with tert- or sec-butyllithium. Monitoring the reaction by 11B NMR has indicated that a boron-ate complex formed in situ is the eventual precursor that converts into aryne near room temperature. The prior formation of the ate complex at a low temperature has enabled us to use various arynophiles, including those bearing base-sensitive groups. The ready availability of the aryne precursors and mutual orthogonality in aryne generation with widely used ortho-silylaryl triflate have enhanced the utility of the method.
Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: A chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols
Sungsuwan, Suttipun,Ruangsupapichart, Nopporn,Prabpai, Samran,Kongsaeree, Palangpon,Thongpanchang, Tienthong
supporting information; experimental part, p. 4965 - 4967 (2011/01/12)
A new chiral derivatizing agent, tetrahydro-1,4-epoxynaphthalene-1- carboxylic acid (THENA), with a represented syn-periplanar disposition of O-Ca-CαO as a part of the bicyclic system to lock the aromatic residue conformation and the availability of an in
Approaches to open fullerenes: Synthesis and kinetic stability of Diels-Alder adducts of substituted isobenzofurans and C60
Chuang, Shih-Ching,Sander, Michael,Jarrosson, Thibaut,James, Scott,Rozumov, Eugene,Khan, Saeed I.,Rubin, Yves
, p. 2716 - 2723 (2008/02/05)
(Chemical Equation Presented) We have examined the reactions of 1,3-disubstituted isobenzofurans with the fullerene C60 in the context of an approach to open a large orifice on the fullerene framework. A variety of substituted isobenzofurans (6a-h), generated from the reaction of 1,4-substituted 1,4-epoxynaphthalenes 3a-h with 3,6-bis(2-pyridyl)-1,2,4,5- tetrazine (4a) or 1,2,4,5-tetrazine (4b), were added to C60 to afford the Diels-Alder adducts 7a-h. The thermal stability of these adducts toward retro-Diels-Alder fragmentation differs greatly in solution from that in the solid state. In solution, the relatively facile retro-Diels-Alder fragmentation of monoadducts 7a and 7c, to give C60 and the free isobenzofurans 6a and 6c, have rate constants (and activation barriers) of k = 9.29 × 10-5 s-1 at 70°C (Ea = 32.6 kcal mol -1) and k = 1.36 × 10-4 s-1 at 40°C (Ea = 33.7 kcal mol-1), respectively, indicating that the addition of isobenzofurans to C60 is readily reversible at those temperatures. In the solid state, thermogravimetric analysis of adduct 7a indicates that its decomposition occurs only within the temperature range of 220-300°C. As a result, these compounds can be stored at room temperature in the solid state for several weeks without significant decomposition but have to be handled within several hours in solution.
Deoxygenetion of 1,4-Epoxy-1,4-dihydroarenes with Enneacarbonyldiiron
Best, Wayne M.,Collins, Peter A.,McCulloch, Ross K.,Wege, Dieter
, p. 843 - 848 (2007/10/02)
1,4-Epoxy-1,4-dihydroarenes are converted in high yields into the corresponding arenes with enneacarbonyldiiron in refluxing benzene solution.
