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Beilstein J. Org. Chem. 2020, 16, 674–680, doi:10.3762/bjoc.16.65
Graphical Abstract
Figure 1: Examples of liquid crystal candidates with negative values for dielectric anisotropy (Δε) [6-10].
Figure 2: Synthetic candidate LC targets 8–11.
Scheme 1: Synthesis of 8. Reagents and conditions: a) TMSCF3, NaI, THF, reflux, 55% [13,14].
Scheme 2: Synthesis of 9. Reagents and conditions: a) NBS, HF·Py, DCM; b) t-BuOK, DCM, 42% in two steps [15]; c) ...
Scheme 3: Synthesis of compound 10. Reagents and conditions: a) NaBH4, MeOH, rt, 45%; b) C4H9OCH=CH2, Pd(TFA)2...
Scheme 4: Synthesis of compounds 11. Reagents and conditions: a) PPh3CH3Br, t-BuOK, diethyl ether, 0 °C to rt...
Figure 3: Theory study exploring the relative energies for different conformers of 11a.
Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144
Figure 1: Structures of trifluoromethyl sulfonyl ether bioactives.
Figure 2: Comparison of log P values of comparative aryl thioether motifs [18].
Figure 3: α,α-Difluoroethyl thioether substrates for metabolism studies.
Scheme 1: Fluorometabolites 6–8 isolated after incubation of 4 with C. elegans. Ratios are the average of thr...
Scheme 2: Putative pathways for (α,α-difluoroethyl)(4-methoxyphenyl)sulfane (4) metabolism.
Scheme 3: C. elegans incubation of 5. Ratios are the average of three incubations.
Scheme 4: Incubation (four times) of oxygen ether 14 with C. elegans, gave 4-acetoxyphenol (15) as the major ...
Beilstein J. Org. Chem. 2017, 13, 728–733, doi:10.3762/bjoc.13.72
Figure 1: The derivatives of all-cis-2,3,5,6-tetrafluorocyclohexane.
Scheme 1: Reagents and conditions: a) Li (2.5 equiv), NH3, t-BuOH (1 equiv), MeI (2 equiv), 3 h, −78 °C, 18 h...
Scheme 2: Reagents and conditions: a) Et3N·3HF (8 equiv), 18 h, 140 °C; b) Tf2O (4 equiv), pyridine, 1 h, 0 °...
Scheme 3: Reagents and conditions: a) Et3N·3HF (8 equiv), 18 h, 140 °C; b) Tf2O (4 equiv), pyridine, 1 h, 0 °...
Scheme 4: Reagents and conditions: a) terephthaloyl chloride (1 equiv), Et3N (4 equiv), DMAP (20 mol %), DCM,...
Figure 2: X-ray structures and crystal packing of compounds 13, 14 and 15.