A convenient synthesis of 4-ethynylphthalic anhydride via 2-methyl-3-butyn-2-ol

Sabourin, Edward T.; Onopchenko, Anatoli

doi:10.1021/jo00173a074

Cited by 63 publications

(32 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Letzteres ist durch Bromierung von Phthals‰ure ( 3 4-Bromophthals‰ure [11]; 65% Ausbeute), Umsetzung mit Ammonium-rhodanid ( 3 4-Bromophthalimid (2) [12]; 84% Ausbeute) und Reaktion mit Ammoniak [13] erh‰ltlich (83% Ausbeute). Die Dehydratisierung des Diamids 3 zum Dinitril 4 gelingt weder mit P 2 O 5 noch mit Acetanhydrid oder SOCl 2 /DMF in befriedigender Weise.…”

Section: Ergebnisse ± 21 (Phthalocyanin-291623-tetrayl)tetrakisunclassified

“…2). Die hohen e-Werte der Q-Banden nehmen von [Cu (7)] zu [Cu (9)] und [Cu (11)] mit zunehmender Phenyl-Substitution am P-Atom (P(OEt)Ph, PPh 2 ) stark zu (Tab. 5, Fig.…”

Section: Ergebnisse ± 21 (Phthalocyanin-291623-tetrayl)tetrakisunclassified

“…Die FAB-MS zeigen den¸berraschenden Befund, dass die Zn-und Cu-Komplexe von 7, das freie Phthalocyanin 9 ebenso wie die Zn-und Cu-Komplexe von 9 neben den Peaks der Monomeren die der Dimeren aufweisen. Im Phthalocyanin 11 sind wie in den Zn-und Cu-Komplexen [Zn (11) …”

Section: Ergebnisse ± 21 (Phthalocyanin-291623-tetrayl)tetrakisunclassified

See 2 more Smart Citations

Tetrakis(diethyl‐phosphonat)‐, Tetrakis(ethyl‐phenylphosphinat)‐ und Tetrakis(diphenylphosphin‐oxid)‐substituierte Phthalocyanine

Märkl¹,

Gschwendner²,

Rötzer³

et al. 2004

Helvetica Chimica Acta

View full text Add to dashboard Cite

Tetrakis(diethyl phosphonate), Tetrakis(ethyl phenylphosphinate)-, and Tetrakis(diphenylphosphine oxide)-Substituted PhthalocyaninesThe title compounds 7, 9, and 11 are obtained by tetramerization of diethyl (3,4-dicyanophenyl)phosphonate (5), ethyl (3,4-dicyanophenyl)phenylphosphinate (8), and 4-(diphenylphosphinyl)benzene-1,2-dicarbonitrile (10). The 31 P-NMR spectra of the phthalocyanines 7, 9, and 11 and of their metal complexes present five to eight signals confirming the formation of four constitutional isomers with the expected C 4h , D 2h , C 2v , and C s symmetry. In the FAB-MS of the Zn, Cu, and Ni complexes of 7 and 9, the peaks of dimeric phthalocyanines are observed. By gel-permeation chromatography, the monomeric complex [Ni (7)] and a dimer [Ni(7)] 2 can be separated. These dimers differ from the known phthalocyanine dimers, i.e., possibly the P(O)(OEt) 2 and P(O)(Ph)(OEt) substituents in 7 and 9 are involved in complexation. The free phosphonic acid complex [Zn (12) (12)], only the peaks of the dimer are present; the ESI-MS confirms the existence of the dimer and the metal-free dimer. In the UV/VIS spectrum of [Zn(12)], the hypsochromic shift characteristic for the known type of dimers from 660 ± 700 nm to 620 ± 640 nm is observed. As in the FAB-MS of [Zn(12)], the free phosphinic acid complex [Zn(13)] shows only the monomer, an ESI-MS cannot be obtained for solubility problems. The UV/VIS spectrum of [Zn(13)] demonstrates the existence of the monomer as well as of the dimer.

show abstract

Section: Ergebnisse ± 21 (Phthalocyanin-291623-tetrayl)tetrakisunclassified

“…2). Die hohen e-Werte der Q-Banden nehmen von [Cu (7)] zu [Cu (9)] und [Cu (11)] mit zunehmender Phenyl-Substitution am P-Atom (P(OEt)Ph, PPh 2 ) stark zu (Tab. 5, Fig.…”

Section: Ergebnisse ± 21 (Phthalocyanin-291623-tetrayl)tetrakisunclassified

See 1 more Smart Citation

Tetrakis(diethyl‐phosphonat)‐, Tetrakis(ethyl‐phenylphosphinat)‐ und Tetrakis(diphenylphosphin‐oxid)‐substituierte Phthalocyanine

Märkl¹,

Gschwendner²,

Rötzer³

et al. 2004

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…O/CH, 6 Infrared and NMR spectra of polymers do not exhibit signals of oxyphenylene fragments, which may principally be formed due to the coupling of the terminal alkynol groups with aryl dihalides by heating the reaction mixture during the second stage.…”

Section: Ochmentioning

confidence: 99%

“…The I3C NMR shows resonances typical of substituted benzene rings at 135,3-121, 6 ppm and resonances at 94,8; 93,9; 91,5; 86,9 ppm due to the carbons of the acetylene units of the polymer '). Additionally, the resonances of carbons from substituents and signals of carbinol end-groups are present (65,7; 31,4) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐catalyzed synthesis of poly(p‐phenyleneethynylene)s

Solomin

Heitz

1994

Macro Chemistry & Physics

View full text Add to dashboard Cite

Poly(ppheny1eneethynylene)s were obtained by reacting 1,4-dihaloarenes with 2-methyl-3-butyn-2-01 in a two-step one-pot process. In the first step a dihaloarene is reacted with two equivalents of 2-methyl-3-butyn-2-01 at room temperature in the presence of an aqueous base. For polycondensatioj a second equivalent of dihaloarene is added and reacted at 100°C. Soluble polymers with M , of 1 -2 . lo4 were obtained. They show blue fluorescence.

show abstract

Trimethylsilylacetylene

Nwokogu¹

2001

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

A convenient synthesis of 4-ethynylphthalic anhydride via 2-methyl-3-butyn-2-ol

Cited by 63 publications

References 0 publications

Tetrakis(diethyl‐phosphonat)‐, Tetrakis(ethyl‐phenylphosphinat)‐ und Tetrakis(diphenylphosphin‐oxid)‐substituierte Phthalocyanine

Tetrakis(diethyl‐phosphonat)‐, Tetrakis(ethyl‐phenylphosphinat)‐ und Tetrakis(diphenylphosphin‐oxid)‐substituierte Phthalocyanine

Palladium‐catalyzed synthesis of poly(p‐phenyleneethynylene)s

Trimethylsilylacetylene

Contact Info

Product

Resources

About