• Title/Summary/Keyword: Wittig Reaction

Search Result 55, Processing Time 0.023 seconds

Studies on Polyphosphazenes-bound Wittig Reactions (포스파젠 고분자를 이용한 Wittig반응에 관한 연구)

  • Kwon, Suk-Ky;Jun, Chang-Lim
    • Applied Chemistry for Engineering
    • /
    • v.5 no.5
    • /
    • pp.843-850
    • /
    • 1994
  • Polyphosphazene-bound Wittig reagents such as $[NP(OC_6H_5)_{1.7}(OC_6H_4P(Ph)_2$=$CHCH_2CH_2CH_3)_{0.3}]_n$ were synthesized by treating $[NP(OC_6H_5)_{1.7}(OC_6H_4Br)_{0.3}]_n$ with n-butyllithium, diphenylchlorophosphine, and n-butyl iodide. Polymeric reactions were carried out according to the reaction conditions with cyclic primers such as [$N_3P_3(OC_6H_5)_5(OC_6H_4P(Ph)_2$)]. The desired alkene and polymer-bound phosphine oxide were prepared successfully by the reaction of polyphosphazene-bound Wittig reagents with benzophenone.

  • PDF

A Convergent Synthetic Study of Biologically Active Benzofuran Derivatives

  • Hu, Kun;Jeong, Jin-Hyun
    • Archives of Pharmacal Research
    • /
    • v.29 no.6
    • /
    • pp.476-478
    • /
    • 2006
  • In order to construct a benzofuran library, we developed a model study of benzbromarone. Synthesis has been achieved in 53% overall yield, starting from phenol via the key intermediate 2-ethylbenzofuran which was afforded by intramolecular Wittig reaction.

Reaction of Phosphorus Ylides with Carbonyl Compounds in Supercritical Carbon Dioxide (초임계 이산화탄소에서의 유기인 일리드와 카르보닐 화합물의 반응)

  • Jeong, Kyung-Il;Kim, Hak-Do;Shim, Jae-Jin;Ra, Choon-Sup
    • Journal of the Korean Chemical Society
    • /
    • v.48 no.1
    • /
    • pp.28-32
    • /
    • 2004
  • The condensation reaction of (benzylene)triphenylphosphoranes with carbonyl compounds in supercritical carbon dioxide was examined. Reactions of (benzylene)phosphoranes (ca. 1 mmol) with several benzaldehydes in a supercritical carbon dioxide (80 $^{\circ}C$, 2,000 psi) containing THF entrainer (5%) in a 24 mL reactor proceed smoothly to yield olefination products in fairly good to excellant yields but slower, compared to reactions in a conventional THF solvent. Generally, phosphoranes that are not substituted with a nitro group show more (Z)-selective reactions with aromatic aldehydes under $scCO_2$ condition than in THF. The reaction of (benzylene)triphenylphosphoranes with 4-t-butylcyclohexanone gave the corresponding olefin compounds with a low conversion under both the supercritical carbon dioxide and the organic THF solvent. Our preliminary study showed the Wittig reaction carries out smoothly in supercritical carbon dioxide medium and also a possibile tunability of this reaction pathway by adding a entrainer. The results would be useful for devising a novel process for the environmentally friendly Wittig reaction.

Synthesis of Fréchet-type Dendrimers with Tripodal Core via Staudinger/Aza-Wittig Reactions (Staudinger/Aza-Wittig 반응에 의한 삼발이 핵을 갖는 Fréchet-type 덴드리머의 합성)

  • Han, Seung Choul;Lee, Jae Wook;Jin, Sung-Ho
    • Polymer(Korea)
    • /
    • v.38 no.3
    • /
    • pp.386-390
    • /
    • 2014
  • Efficient stitching methods for the synthesis of tripodal Fr$\acute{e}$chet-type dendrimers containing secondary amine as a connector were elaborated. The synthetic strategy involved Staudinger/aza-Wittig reactions (new click reaction) between tripodal tris(azides) and aldehyde-dendrons in toluene in the presence of triphenylphosphine and followed by the reduction of imine intermediates. The tripodal core (1,3,5-tris-(3-azido-propoxy)-benzene) was chosen to serve as the azide functionalities for dendrimer growth. 1,3,5-Tris-(3-azido-propoxy)-benzene was stitched with the aldehyde-functionalized Fr$\acute{e}$chet-type dendrons via Staudinger/aza-Wittig reactions leading to the formation of the corresponding Fr$\acute{e}$chet-type dendrimers in high yields.

Theoretical Studies on the Gas-Phase Wittig-Oxy-Cope Rearrangement of Deprotonated Diallyl Ether

  • Kim, Chang-Kon;Lee, Ik-Choon;Lee, Hai-Whang;Lee, Bon-Su
    • Bulletin of the Korean Chemical Society
    • /
    • v.12 no.6
    • /
    • pp.678-681
    • /
    • 1991
  • The Wittig-oxy-Cope rearrangements of deprotonated diallyl ether, I, $CH_2={\bar{C}}H-CH-O-CH_2-CH=CH_2$, have been investigated theoretically by the AM1 method. A two step mechanism forming a Wittig product ion, II, $(CH_2=CH)$ $(CH_2=CH-CH_2)$ $CHO^-$, through a radical-pair intermediate was found to provide the most favored reaction pathway in the Wittig rearrangement. The subsequent oxy-Cope rearrangement from species II also involves a two step mechanism through a biradicaloid intermediate. The intramolecular proton transfer in I (to form $CH_2=CH-CH_2-O-{\bar{C}}H-CH=CH_2$) is a higher activation energy barrier process compared to the Wittig and oxy-Cope rearrangements and is considered to be insignificant. These results are in good agreement with the condensed-phase as well as gas-phase experimental results.

Synthesis and Characterization of Poly[9,10-diphenylanthracene-4$^\prime$, 4$^\prime^\prime$-ylenevinylene-3,6-(N-2-ethylhexyl)carbazole]

  • Kim, Yun Mi;Park, Gi Min;Gwon, Sun Gi
    • Bulletin of the Korean Chemical Society
    • /
    • v.22 no.9
    • /
    • pp.975-978
    • /
    • 2001
  • A novel poly[9,10-diphenylanthracene-4',4"-ylenevinylene-3,6-(N-2-ethyl hexyl)carbazole] containing alternate diphenylanthracene and carbazole unit was synthesized by the Wittig reaction. The obtained polymer was soluble in common organic solvents and thermally stable up to 380 $^{\circ}C.$ The polymer gives rise to bright blue fluorescence both in solution and in thin solid films. The light emitted from the device (ITO/polymer/Al) was greenish-blue in color and clearly visible in daylight.

Synthesis of Blue Emitting Materials for Organic Light Emitting Device (유기발광디바이스용 청색발광재료의 합성)

  • Chung, Pyung Jin;Cho, Min Ju
    • Applied Chemistry for Engineering
    • /
    • v.16 no.6
    • /
    • pp.755-759
    • /
    • 2005
  • This study was based on organic electroluminescence display. Especially, DPAVBi, AVBi and DPVBi for the emitting materials were synthesized by Wittig, Wittig-Horner reaction. This reaction was conducted between phosphorous ylide and 4-(diphenylamino)benzaldehyde, 9-anthraldehyde and benzophenone. The structural property of reaction products were analyzed by FT-IR, $^1H-NMR$ spectroscopy and thermal stability, reactivity and PL property were analyzed by melting point, yield and emission spectrum, respectvely. The photoluminescence spectra of a pure DPAVBi, AVBi and DPVBi were observed at approximately 445nm, 484nm and 450nm, respectively. In this study, it was known that DPAVBi, AVBi, DPVBi had a different reaction properties according to stability of ${\alpha}$-position carbonyl group of the aldehyde, ketone.