Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• /chloroform 95:5, 1.0 mL/min, 40 °C; (S)-3a: tR = 7.25 min, (R)-3a: tR = 14.12 min, UV detection at 250.0 nm. Compound 3b: Synthesized similarly to 3a using 4-tert-butylphenol. Purified by silica gel column chromatography (eluent: hexane/EtOAc 4:1) and GPC to give the title compound as white solid; (S)-3b

Synthesis and post-functionalization of alternate-linked-meta-para-[2ⁿ.1ⁿ]thiacyclophanes

• Wout De Leger,
• Koen Adriaensen,
• Koen Robeyns,
• Luc Van Meervelt,
• Joice Thomas,
• Björn Meijers,
• Mario Smet and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2190–2197, doi:10.3762/bjoc.14.192

• [12], we now report the development of an alternate meta-para-thiacyclophane which could be post-functionalized. The precursors 2,6-bis(chloromethyl)-4-tert-butylphenol (4) and commercially available 4,4’-thiobisbenzenethiol (5) were chosen as the biselectrophile and bisnucleophile, respectively [27

• ], less synthetic work has been performed on the synthesis of sulfur-linked cyclophanes with an alternating meta-para-bridge [26]. Herein we report a one-pot macrocyclization of meta-para-bridged thiacyclophanes by means of a substitution reaction between the biselectrophile 2,6-bis(chloromethyl)-4-tert

• -butylphenol (4) and the bisnucleophile 4,4’-thiobisbenzenethiol (5). Either the [2 + 2] adduct 6 or the [3 + 3] adduct 7 were selectively obtained by varying the reaction conditions. Post-functionalization of the phenolic moieties was successfully performed. Alternate-linked-meta-para-[22.12]thiacyclophane 6

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• the DW tested, showed that the polymer is able to adsorb 4-tert-butylphenol, 1,2-dichloroethane and chloroform, but also APs and the organo-halogenated compounds (represented by the AOX parameter). For the retention of APs, no difference was noted between 4NP, 4nNP and 4tOP. Heavy PAHs were better

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• with β-cyclodextrin derivatives. Since 4-alkylphenyl moieties are good guests for ß-cyclodextrin [37][38], we were encouraged to use 4-tert-butylphenol as well as 4-tert-octylphenol and modify them with mercapto groups. By doing so, well-defined PDEAAm end-group labeled polymers can be obtained by

• Table 1. Exemplarily, Figure 1 shows a section of the MALDI–TOF spectrum of polymer 8b confirming a high degree of 4-tert-butylphenol end-group functionalization. Just single series of peaks with a peak separation of 127.1 which corresponds to the mass of DEAAm plus the proposed end-group (224.1) and

• remarkable effect on the cloud point of the polymers bearing a 4-tert-octylphenol end-group compared to the 4-tert-butylphenol end-group could be expected. Consequently hydrophobic interactions must play an important role for this effect. Regarding Figure 4 and Table 2 the hydrophobic interactions seem to be

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

• Adam Mondrzyk,
• Beate Mondrzik,
• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• of a copolymer of 4-tert-butylphenol and 4-ferrocenylphenol by horse radish peroxidase (HRP) in the presence of H2O2 in a 1,4-dioxane/water system is described. Furthermore, polymer-analogous alkylation of the free hydroxy groups and subsequent click reaction with mono-6-azido-6-desoxy-β-cyclodextrin

• (N3-β-CD) was carried out. The formation of inter- and intramolecular inclusion complexes was investigated by DLS measurement. Keywords: copolymer; ß-cyclodextrin; enzymatic polymerization; 4-ferrocenylphenol; polyphenol; 4-tert-butylphenol; horseradish peroxidase; HRP oxidative coupling; inclusion

• phenols in water/organic-solvent systems in the presence of hydrogen peroxide. In recent studies it was demonstrated that several para-substituted phenols, i.e., 4-tert-butylphenol, can be polymerized with HRP in high yield and relatively high molecular weights [13]. Also several polyphenols with further

Fifty years of oxacalix[3]arenes: A review

• Kevin Cottet,
• Paula M. Marcos and
• Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

• heating 2,6-bis(hydroxymethyl)-4-tert-butylphenol [11]. Elemental analysis gave an empirical formula of C12H16O2 and molecular weight determinations gave values corresponding to a trimer. Despite interest in novel phenol–formaldehyde polymers and macrocycles and characterization of 3a in 1979 [13], it

• ]. Although not discussed by Gutsche, both cyclotrimers and tetramers are usually formed by this method and, in 1991, Vicens and Zerr performed a thermal dehydration of 2,6-bis(hydroxymethyl)-4-tert-butylphenol in xylene under reflux allowing them to isolate p-tert-butyloctahomotetraoxacalix[4]arene (4a