Olefin Synthesis with Anils

Fletcher, Ian; Siegrist, A. E.

doi:10.1016/s0065-2725(08)60843-0

Cited by 29 publications

(7 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Therefore, we chose chromophore 4 as one of the repeating units of polymer 7 that would be expected to exhibit the desired properties and also provide synthetic versatility. Chromophore 4 was prepared by the so-called “Anil Synthesis”, which involves the condensation of Schiff's bases with methyl groups. − The Anil Synthesis proceeds rapidly with molecules that have an electron-withdrawing group in the para position to the methyl group, however the reaction proceeds even without activating groups. We found that under modified reaction conditions, using longer reaction times, higher reaction temperatures, and an excess of Schiff's bases and t -BuOK, methyl groups even with electron-donating substituents in their para positions can be completely converted into styryl groups by the Anil Synthesis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of a Blue Light Emitting Polymer Containing Both Hole and Electron Transporting Units

Lü¹,

Hlil²,

Sun³

et al. 1999

Chem. Mater.

View full text Add to dashboard Cite

A luminescent bipolar polymer 7, consisting of a Ar 3 N-stilbene moiety and an oxadiazole moiety, has been synthesized. A smooth and dense thin film of polymer 7 is easily obtained by spin-coating from its chloroform solution. This film exhibits a strong fluorescence in the blue. More importantly, polymer 7 possesses an extremely high thermal stability with a 5% weight loss temperature of 480 °C under nitrogen, and a relatively high glass transition temperature (T g ) of 239 °C. Single-layer EL devices fabricated with this polymer emitted low intensity blue light after a turn-on voltage of 5 V. The brightness, luminance, and apparent quantum efficiency of these devices are drastically improved by adding, between polymer 7 and the Al cathode, another spin-coated polymer layer containing an oxadiazole derivative.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of a Blue Light Emitting Polymer Containing Both Hole and Electron Transporting Units

Lü¹,

Hlil²,

Sun³

et al. 1999

Chem. Mater.

View full text Add to dashboard Cite

show abstract

“…26,27,[29][30][31] The oxazolecontaining compounds were found to be interesting luminescent materials, [32][33][34][35] whitening agents, laser dyes, and optical fiber sensors. [36][37][38] Here, we demonstrate that a bipyridyl Ru(II) complex containing Hbopip acted as a pH-induced off-onoff luminescence switch with a large luminescence on-off ratio of 20 over a narrow acidic region, and a strong DNA intercalator with a large binding constant of (1.2 ( 0.3) × 10 7 M -1 in buffered 50 mM NaCl. 39 and 1,10-phenanthroline-5,6-dione 40 were prepared by the literature routes.…”

Section: Introductionmentioning

confidence: 82%

Ruthenium(II) Complex of Hbopip: Synthesis, Characterization, pH-Induced Luminescence “Off−On−Off” Switch, and Avid Binding to DNA

et al. 2006

View full text Add to dashboard Cite

A novel ruthenium(II) complex of [Ru(bpy)2(Hbopip)](ClO4)2 (in which bpy=2,2'-bipyridine, Hbopip=2-(4-benzoxazolyl)phenylimidazo[4,5-f][1,10]phenanthroline) was synthesized and characterized. The spectrophotometric pH titrations of the complex showed that it acted as a pH-induced luminescence "off-on-off" switch: a luminescence off-on switch with a luminescence enhancement factor of IpH=3.0/IpH=1.0=20 occurring over a narrow pH range of 1.00-3.00 plus a luminescence on-off switch with a luminescence enhancement factor of 3 over a pH range of 3.20-9.40. The excited-state ionization constant of the complex derived, pKa1*=3.06, is 1.36 pKa units greater than the ground-state pKa1=1.70, and pKa2*=5.01 and pKa3*=8.22 are comparable to the ground-state pKa2=5.23 and pKa3=8.22, respectively. The complex avidly bound to calf thymus DNA with a large binding constant of (1.2+/-0.3)x10(7) M-1 in buffered 50 mM NaCl, as evidenced by UV-vis and luminescence titrations, steady-state emission quenching by [Fe(CN)6]4-, DNA competitive binding with ethidium bromide, viscosity measurements, and DNA melting experiments.

show abstract

“…We also investigated the 'anil synthesis' (cf. [ 15])'), which works well with acidic Me groups at aromatic or heteroaromatic hydrocarbons, for the preparation of azulenes with styryl substituents at the seven-membered ring.…”

mentioning

confidence: 99%

New Results in the Synthesis of Styrylazulene Derivatives: Application of the ‘Anil synthesis’ to the preparation of azulenes substituted with styryl groups at the seven‐membered ring

Briquet

Hansen

1994

Helvetica Chimica Acta

View full text Add to dashboard Cite

The synthesis of 4,6,8-trimethyl-l-[(E)-4-R-styryl]azulenes 5 (R=H, MeO, Cl) has been performed by Wittig reaction of 4,6,8-trimethylazulene-1-carbaldehyde (1) and the corresponding 4-(R-benzyl)(triphenyl)phosphonium chlorides 4 in the presence of EtONa/EtOH in boiling toluene (see Table 1 ). In the same way, guaiazulene-3carbaldehyde (2) as well as dihydrolactaroviolin (3) yielded with 4a the corresponding styrylazulenes 6 and 7, respectively (see Table 1). It has been found that 1 and 4b yield, in competition to the Witfig reaction, alkylation products, namely 8 and9, respectively (cf. Scheme I ). Thereaction of4,6,8-trimethylazulene(l0) with 4b in tolueneshowed that azulenes can, indeed, be easily alkylated with the phosphonium salt 4b. 4,6,8-Trimethylazulene-2carbaldehyde (12) has been synthesized from the corresponding carboxylate 15 by a reduction (LiAlH,) and dehydrogenation (MnOz) sequence (see Scheme 2). The Swern oxidation of the intermediate 2-(hydroxy-methy1)azulene 16 yielded only 1,3-dichloroazulene derivatives (cf: Scheme 2). The Witrig reaction of 12 with 4a and 4b in the presence of EtONa/EtOH in toluene yielded the expected 2-styryl derivatives 19a and 19b, respectively (see Scheme 3 ) . Again, the yield of 19b was reduced by a competing alkylation reaction of 19b with 4b which led to the formation of the I-benzylated product 20 (see Scheme 3 ) . The 'anil synthesis' of guaiazulene (21) and the 4-R-benzanils 22 (R=H, MeO, C1, Me,N) proceeded smoothyl under standard conditions (powered KOH in DMF) to yield the corresponding 4-[(E)-styryl]azulcne derivatives 23 (see Table 4 ) . In minor amounts, bis(azulen-4-yl) compounds of type 24 and 25 were also formed (see Table 4 ) . The 'anil reaction' of 21 and 4-NOZC,H,CH=NC,H, (22e) in DMF yielded no corresponding styrylazulene derivative 23e. Instead, (E)-1,2-bis(7isopropyl-1-methylazulen-4-yl)ethene (27) was formed (see Scheme 4 ) . The reaction of 4,6,8-trimethylazulene (10) and benzanil (22a) in the presence of KOH in DMF yielded the benzanil adducts 28 to 31 (cf: Scheme 5 ) . Their direct base-catalyzed transformation into the corresponding styryl-substituted aznlenes could not be realized (qf. Scheme 6). However, the transformation succeeded smoothly with KOH in boiling EtOH after N-methylation (cfi Scheme 6).

show abstract

Olefin Synthesis with Anils

Cited by 29 publications

References 35 publications

Synthesis and Characterization of a Blue Light Emitting Polymer Containing Both Hole and Electron Transporting Units

Synthesis and Characterization of a Blue Light Emitting Polymer Containing Both Hole and Electron Transporting Units

Ruthenium(II) Complex of Hbopip: Synthesis, Characterization, pH-Induced Luminescence “Off−On−Off” Switch, and Avid Binding to DNA

New Results in the Synthesis of Styrylazulene Derivatives: Application of the ‘Anil synthesis’ to the preparation of azulenes substituted with styryl groups at the seven‐membered ring

Contact Info

Product

Resources

About