20056-63-7Relevant articles and documents
Iron(III)-Catalyzed Ortho-Preferred Radical Nucleophilic Alkylation of Electron-Deficient Arenes
Yu, Fei,Wang, Ting,Zhou, Huan,Li, Yajun,Zhang, Xinhao,Bao, Hongli
supporting information, p. 6538 - 6541 (2017/12/26)
The untraditional iron-catalyzed, ortho-preferred, radical alkylation of electron-deficient (hetero)arenes is reported. A variety of electron-deficient arenes were shown to react with various primary alkyl sources, producing the alkylated (hetero)arenes in good yields. This reaction might be an alkyl radical, nucleophilic aromatic substitution reaction, rather than the traditional electrophilic Friedel-Crafts reaction. HOMO-LUMO analysis and DFT studies on the key transition states underlying the regioselectivity are consistent with the observed reactions and the conclusions.
Design of liquid crystalline block molecules with nonconventional mesophase morphologies: Calamitic bolaamphiphiles with lateral alkyl chains
Koelbel,Beyersdorff,Xiao Hong Cheng,Tschierske,Kain,Diele
, p. 6809 - 6818 (2007/10/03)
Novel bolaamphiphiles, consisting of a biphenyl rigid core, polar 2,3-dihydroxypropoxy groups at each terminal end, and an additional long alkyl chain in a lateral position have been synthesized. The structures of these ternary block molecules were systematically changed by variation of the length and position of the alkyl chain, by introduction of additional spacer units between one of the 2,3-dihydroxypropyl groups and the rigid core, and by replacement of one of the 2,3-dihydroxypropoxy groups by a single hydroxy group. The influence of these structural variations on the liquid crystalline properties of these new materials was investigated by polarized-light microscopy, differential scanning calorimetry, and X-ray diffraction. These investigation have shown that, by elongation of the lateral chain, a transition from a smectic monolayer structure (SmA1) via a strongly distorted layer structure (SmA+), a centered rectangular columnar phase (Colr/c2mm) and a noncentered rectangular columnar phase (Colr/p2gg) to a hexagonal columnar phase (Colh/p6mm) takes place. Elongation of the bolaamphiphilic core leads to the loss of the columnar phases, which are replaced by smectic phases, whereas reduction of its length favors the hexagonal columnar phase. This phase sequence is explained as a result of the microsegregation of the lateral alkyl chains from the rigid aromatic cores. The segregated alkyl chains are organized in columns that interrupt the smectic layers. The hydrogen bonding keep the bolaamphiphilic cores fixed end to end, so that they form networks of cylinders around the lipophilic columns. The space required by the alkyl chains with respect to the length of the bolaamphiphilic cores is restricted and largely determines the geometry of the cylinders, which leads to the observed phase sequence. The obtained mesophase morphologies, built up by three distinct sets of subspaces, are related to morphologies of some ternary block copolymers. Furthermore, the investigated compounds represent a novel class of materials, capable of forming supramolecular columnar mesophases.
Long Chain Alkyl Phenols from the Liverwort Schistochila Appendiculata
Asakawa, Yoshinori,Masuya, Toru,Tori, Motoo,Campbell, Ella O.
, p. 735 - 738 (2007/10/02)
3-Undecyl phenol, 6-undecyl salicylic acid and potassium 6-undecyl salicylate were isolated from the New Zealand liverwort Schistochila appendiculata. 3-Tridecyl and 3-pentadecyl phenol, 6-tridecyl and 6-pentadecyl salicylic acid, potassium 6-tridecyl and 6-pentadecyl salicylate and 6-undecyl catechol were also detected in the same species.The chemical constitution of S. appendiculata is quite similar to that of the brown algae Caulocystis species, and of the higher plants Ginkgo biloba and some of the Anacardia species.The allergic reaction brought on by S. appendiculata might be due to the presence of these phenolic compounds.Key Word Index - Schistochila appendiculata; Jungermanniales; Hepaticae; long chain alkyl phenols; 3-undecyl, 3-tridecyl, 3-pentadecyl phenols; 6-undecyl, 6-tridecyl, 6-pentadecyl salicylic acids; potassium 6-undecyl, 6-tridecyl, 6-pentadecyl salicylates; 6-undecyl catechol; allergy; chemosystematics.
