Nitro Musks. I. Isomers, Homologs, and Analogs of Musk Ambrette

Carpenter, M. S.; Easter, W. M.; Wood, Tabitha E.

doi:10.1021/jo01144a011

Cited by 81 publications

(32 citation statements)

References 7 publications

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“…Both intramolecular H-bonding and repulsion of HMPA are expected to diminish or disappear, hence the sizable non-zero values of K eq /H for (5), (6), and (7). Consistent with the intramolecular H-bonding hypothesis, as also shown in Table 5, the δ values of all these protons are less than 9.0, except for (25). It is interesting to compare compounds 22, 29, and 30.…”

Section: 35-trinitrobenzene and Steric Effectssupporting

confidence: 79%

Formation constants in C–H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Lorand¹

2014

Arkivoc

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Formation constants (K eq ) have been measured using 1 H NMR for H-bond complexes with HMPA in CCl 4 of 35 aromatic compounds variously substituted with cyano, nitro, and trifluoromethyl groups; several compounds contained F and Cl. The three strongly polar groups enhance H-bonding significantly, usually in the order NO 2 > CN > CF 3 ; all are superior to Cl and F. 1,3,5-Trinitrobenzene fails to H-bond at all; however, TNT, its tert-butyl analog, and trinitro-m-xylene show significant K eq values. Coplanarity of nitro groups with the ring blocks approach of HMPA, probably via intramolecular H-bonds. The buttressing effect is evident in some crowded compounds.

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Section: 35-trinitrobenzene and Steric Effectssupporting

confidence: 79%

Formation constants in C–H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Lorand¹

2014

Arkivoc

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“…(15).--A mixture of the methyl ether (15) (290 mg), manganese dioxide (0.6 g), and 30% sulphuric acid (5 ml) was stirred vigorously for 8.5 h at 62 0C. 28 After having cooled, the mixture was extracted with ether and the extract was worked up in the usual way to yield a crude product. The aldehyde (17) (17).-The aldehyde (17) (145 mg) and palladium-carbon powder (10% palladium) (5 mg) were heated under nitrogen for 1.5 h at 200-210"C. 29 After having cooled, the reaction mixture was dissolved in ether and the catalyst was removed by filtration.…”

Section: -Bromoherbertenementioning

confidence: 99%

“…Even refluxing the diol (25) with benzene containing a catalytic amount of toluene-psulphonic acid (PTSA) produced the cyclic ether (27). Next, when the cyclic ether (27) was subjected to reaction with aluminium trichloride and ethanethi01,~~ the hydroxy thioether (28), C, ,H2,0S, was fortunately produced in a higher yield (see Scheme 5). Then, formation of the phenol (2), C15H22O, was achieved by reduction of the hydroxy thioether (28) with Raney nickel.…”

mentioning

confidence: 99%

Structures of ent-herbertane sesquiterpenoids displaying antifungal properties from the liverwort Herberta adunca

Matsuo¹,

Yuki²,

Nakayama³

1986

J. Chem. Soc., Perkin Trans. 1

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Several aromatic sesquiterpenoids displaying antifungal properties have been isolated from the liverwort Herberta adunca together with a mother hydrocarbon with a novel irregular sesquiterpene skeleton, entherbertane, and their structures and absolute configurations have been determined on the basis of extensive degradation reactions and spectroscopic evidence. The biological activity is also described. ' B. cinerea R. solani P. debaryanum * B. cinerea R. solani P. debaryanum * B . cinerea R. solani ~ P. debaryanum Concentration (p.p.m.)

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“…[33] This compound was subsequently converted to 1-bromomethyl-4-tert-butyl-2-nitrobenzene as described in [34] . Syntheses of starting piperazine-based ligands 1a and 1b were performed according to the published procedures [8,9] (Scheme 1).…”

Section: Preparation Of Starting Materialsmentioning

confidence: 99%

Piperazine-Based N4-Type 16-Membered Macroheterocycles and Their Nickel(II) Complexes

Вацадзе¹,

Krut’ko²,

Blake³

et al. 2017

MHC

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Square-planar diamagnetic nickel(II) complexes S. Z. Vatsadze et al. конформация сохраняется и в растворе, однако макроцикл оказался конформационно гибким -он подверга-ется вырожденной интерконверсии с активационным барьером 41.9±0.8 кДж/моль.Ключевые слова: 16-Членные макрогетероциклы, диамагнитные комплексы никеля(II), позитронно-эмиссионная томография, рентгеновская дифракция, ЯМР спектроскопия, конформационный анализ. one down), even for the four-coordinate complexes with no additional axial donor ligand(s). We envisaged that such a conformation might, in the long term, allow for asymmetric synthetic applications for metal-ligand multiply-bonded complexes containing such ligands. Finally, we noted that the coordination chemistry of piperazines [10,11] and their open-chain [8,[12][13][14][15][16] and macrocyclic [17][18][19][20][21][22][23] derivatives has only been developed for late transition metals.The coordination and supramolecular, as well as synthetic, chemistry of piperazine-based molecules is a currently emerging area. This activity is defined, first of all, by the conformational features of the piperazine ring. For example, in a recent paper Stucchi et al. reported the application of piperazine-based peptidomimetics.[24] Although Thirunarayanan et al. reported the complexation properties of piperazinophanes, [25] they did not adequately address the conformational behavior of the ring. The other direction of the application of piperazine-based ligands is the use of titanium complexes designed for the ring-opening polymerization of rac-lactide.[26] Piperazine-based macrocycles are known to form supramolecular tubular structures [27] and promising receptor-mimic phanes.[28]In the present work we have synthesized and studied the crystal and solution structures of two Cu(II) and four Ni(II) complexes with N 4 -type ligands (Figure 2).For 1a and 1b it has been shown that anilinic protons could be easily changed for SiMe 3 groups by the action of TMSCl/DABCO (trimethylsilyl chloride / 1,4-diazabicyclo-[2.2.2]octane).[9] The already-mentioned interesting feature of the ligands 1a and 1b in their Ni, Cu, Pd and Ti complexes studied so far, [8,9] is the non-planar, pseudo-C 2 symmetric (transoid) conformation that they adopt.Complexes 5a and 5b were included in this study because they contain the imine nitrogen that favors strong Ni-N bonding due to back-donation from Ni to the π* N=C orbital. Another feature of cyclic diimine ligands 4a and 4b is the rigid xylylidene bridge between imine nitrogens, which creates an additional reason for the cisoid conformation. This conformation is of particular interest for catalysis due to one

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Nitro Musks. I. Isomers, Homologs, and Analogs of Musk Ambrette

Cited by 81 publications

References 7 publications

Formation constants in C–H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Formation constants in C–H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Structures of ent-herbertane sesquiterpenoids displaying antifungal properties from the liverwort Herberta adunca

Piperazine-Based N4-Type 16-Membered Macroheterocycles and Their Nickel(II) Complexes

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