scholarly journals 1-[4-{1,1′,1″,1‴,1′′′′-(1,3-Cyclopentadien-1,2,3,4,5-pentayl)pentakis}]-(4,1-phenylen)-alkanone und -benzoesäure pentaalkylester und deren Natrium- und Thallium(I)-Komplexe / 1-[4-{1,1′,1″,1‴,1′′′′-( 1,3-Cyclopentadiene-1,2,3,4,5-pentayl)pentakis}]-(4,1-phenylene)-alkanones and -benzoic Acid Pentaalkyl Esters and their Sodium- and Thallium(I) Complexes

1992 ◽  
Vol 47 (9) ◽  
pp. 1281-1289 ◽  
Author(s):  
Herbert Schumann ◽  
Homa Kucht ◽  
Andreas Kucht
Keyword(s):  
Benzoic Acid ◽  
Nmr Spectra ◽  
Sodium Salts ◽  
Acyl Chlorides ◽  
New Compounds ◽  
C Nmr

Pentaphenylcyclopentadiene (1) reacts with acyl chlorides RC(O)Cl (R = CH3, C3H7, C5H11, C7H15) with formation of the corresponding [(cyclopentadiene pentayl)pentakis] (1,4-phenylene) alkanones C5H(C6H4C(O)R-4)5 (2a, 2c, 2d and 2e). 2 a reacts with KOCl in water/dioxane to yield C5Cl(C6H4C(O)OH-4)5 (3), which after reaction with C2H5OH and C5H11OH gives the pentaesters C5Cl(C6H4C(O)OR-4)5 (4b and 4d), and after reaction with (CH3)3SnH the corresponding [(cyclopentadiene pentayl)pentakis] benzoic acid pentaalkyl esters C5H(C6H4C(O)OR-4)5 (5b and 5d). Reaction of 2a, 2c, 2d, 2e and 5b with NaNH2 results in the formation of the sodium salts Na[C5(C6H4C(O)R-4)5] (6a, 6c, 6d and 6e) and Na[C5(C6H4C(O)OC2H5-4)5] (7). 2a, 2c, 2d, 2e, 5b and 5d react with TlOC2H5 to give the thallium(I) derivatives Tl[C5(C6H4C(O)R-4)5] (8a, 8c, 8d, 8e) and Tl[C5(C6H4C(O)OR-4)5] (9b and 9d). The 1H and 13C NMR spectra of the new compounds are reported and discussed.

Configuration of sodium salt and preparation of sulphonates and carboxylates of (E)- and (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone

1984 ◽  
Vol 49 (8) ◽  
pp. 1907-1913 ◽  
Author(s):  
Jaroslav Jonas
Keyword(s):  
Solid State ◽  
Sodium Salt ◽  
Nmr Spectra ◽  
Sulphonic Acid ◽  
Sodium Salts ◽  
Acyl Chlorides ◽  
Acid Anhydrides ◽  
High Yields ◽  
C Nmr

The sodium salt of 3-(hydroxymethylene)dihydro-2(3H)-furanone (I) can be obtained in solid state in the form of (Z)-isomer, or their mixture, whereas in solutions it only exists in the form of (E)-isomer. Reactions of these sodium salts with sulphonyl or acyl chlorides or sulphonic acid anhydrides give the respective (E)- and (Z)-sulphonates or carboxylates of 3-(hydroxymethylene)dihydro-2(3H)-furanone in high yields and purity. Configuration of the sodium salt isomers has been confirmed by their IR and 12C NMR spectra in solid state, that of the isomeric sulphonates and carboxylates has been confirmed by their 1H and 13C NMR spectra in solution.

1,4-Bis(4-acylphen-1 -yl) 1,3-cy clopentadiene und 1,2,3,4-Tetra(4-alkylphen-1-yl)-1,3-cyclopentadiene und deren Natrium-, Thallium(I)- und Eisen(II)-Komplexe / 1,4-Bis(4-acylphen-1-yl)-1,3-cyclopentadienes and 1,2,3,4-Tetra(4-alkylphen-1-yl)- 1,3-cyclopentadienes and their Sodium, Thallium (I) and Iron(II) Complexes

1997 ◽  
Vol 52 (1) ◽  
pp. 45-52
Author(s):  
Herbert Schumann ◽  
Alexander Lentz
Keyword(s):  
Nmr Spectra ◽  
Acyl Chlorides ◽  
Sodium Complexes ◽  
New Compounds ◽  
C Nmr

1,4-Diphenyl-1,3-cyclopentadiene reacts with acyl chlorides RC(O)Cl (R = CH3 (a), C5H11 (c )) to form the corresponding 1,4-bis(4-acylphen-1-yl)-1,3-cyclopentadienes C5 H4 (C6H4 C(O)R)2 (1a, 1c), which upon treatment with NaNH2 or with TlOC2H5 afford the corresponding sodium complexes Na[C5H3 (C6H4C(O)R)2] (2a, 2c) or thallium(I) derivatives Tl[C5H3 (C6H4C(O)R)2] (3a, 3c). The reaction of 1,1′,3,3′-tetraphenylferrocene with CH3C(O)Cl results in the formation of Fe[C5H2 {C(O)CH3} {(C6H4C(O)CH3)2}]- [C5H3 {(C6H4C(O)CH 3)2}] (5), whereas 2c and FeCl2 give Fe[C5H3(C6H4C(O)C5H11)2]2 (4c). The all-para-acylated tetraphenylcyclopentadienes C5H2 (C6H4C(O)R)4 (R = CH3 (a), C3H7 (b)) react with K[N2H4OH] to produce the ligands C5H2(C6H4CH2R)4 (6a, 6b), which undergo reactions with NaNH2 and TlOC2H5 to yield the sodium and thallium(I) salts, Na[C5H2(C6H4CH2R)4] (7a, 7b) and Tl[C5H2(C6H4CH2R)4] (8a, 8b), respectively. 7a and 7b react with FeCl2 to produce the corresponding ferrocenes Fe[C5H(C6H4CH2R)4 ]2 (9a, 9b). The 1H and 13C NMR spectra of the new compounds are reported and discussed

1.2.3.4.5-Penta(4-alkylphen-1-yl)-1,3-cyclopentadiene und deren Natrium-, Indium(I)- und Thallium(I)-Komplexe / 1.2.3.4.5-Penta(4-alkylphen-1-yl)-1,3-cyclopentadienes and their Sodium-, Indium(I)- and Thallium(I) Complexes

1994 ◽  
Vol 49 (12) ◽  
pp. 1717-1724 ◽  
Author(s):  
Herbert Schumann ◽  
Alexander Lentz
Keyword(s):  
Nmr Spectra ◽  
Sodium Salts ◽  
New Compounds ◽  
C Nmr

(Cyclopentadiene pentayl)pentakis[(1,4-phenylene)alkanones] C5H(C6H4C(0)R-4)5 (R=CH3 (1a), C3H7 (1b), C5H7 (1c), C7H15 (1d)) react with N2H4(H2O)/KOH or Et3SiH/ CF3COOH to yield the oxygen free ligands C5H(C6H4CH2R-4)5 (2a, 2b, 2c and 2d), which after reaction with NaNH2 give the corresponding sodium salts Na[C5(C6H4CH2R-4)5] (3a, 3b, 3c and 3d). The sodium salts Na[C5(C6H4C(O)R-4)5] (R=CH3 (4a), C5H11 (4c) and 3a react with InCl to give In[C5(C6H4C(O)R-4)5] (5a, 5c) and In[C5(C6H4CH2R-4)5] (6a). 2a, 2b, 2c and 2d react with TlOC2H5 yielding Tl[C5(C6H4CH2R-4)5] (7a, 7b, 7c and 7d). The 1H and 13C NMR spectra of the new compounds are reported and discussed.

The biosynthesis of ephedrine

1989 ◽  
Vol 67 (6) ◽  
pp. 998-1009 ◽  
Author(s):  
Gunnar Grue-Sørensen ◽  
Ian D. Spenser
Keyword(s):  
Carbon Atom ◽  
Benzoic Acid ◽  
Pyruvic Acid ◽  
Nmr Spectra ◽  
Carbon Skeleton ◽  
Resonance Spectroscopy ◽  
Methyl Group ◽  
Acid Incorporation ◽  
Group A ◽  
C Nmr

It is shown by 13C nuclear magnetic resonance spectroscopy that the labelled C2 fragment of [2,3-13C2]pyruvic acid is transferred intact into the C-methyl group and the adjacent carbon atom of the Ephedra alkaloids, norephedrine, ephedrine, norpseudoephedrine, and pseudoephedrine, in growing plants of Ephedragerardiana. This finding serves to identify pyruvate as the elusive precursor of the aliphatic C2 terminus of the skeleton of the alkaloids. In earlier experiments with C-labelled substrates, label from [3-14C]pyruvic acid was incorporated mainly, but not exclusively, into the C-methyl group of ephedrine, and label from [2-14C]pyruvate was incorporated similarly into the carbon atom adjacent to the C-methyl group. A C6–C1 unit related to benzaldehyde or benzoic acid has long been known to generate the benzylic fragment of the carbon skeleton of the Ephedra alkaloids. It is likely that the carbon skeleton of ephedrine is generated from pyruvate and either benzaldehyde or benzoic acid, by a reaction analogous to the formation of acetoin or diacetyl from pyruvate and acetaldehyde or acetic acid, respectively. Keywords: biosynthesis of ephedrine, Ephedra alkaloids, 13C NMR spectra, ephedrine, biosynthesis of pyruvic acid, incorporation into ephedrine13C NMR spectra.

Bis[dicarbonyl(cyclopentadienyl)ruthenium(I)] Komplexe / Bis[dicarbonyl(cyclopentadienyl)ruthenium(I)] Complexes

2002 ◽  
Vol 57 (9) ◽  
pp. 1017-1026 ◽  
Author(s):  
Herbert Schumann ◽  
Susanne Stenz ◽  
Frank Girgsdies ◽  
Stefan H. Mühle
Keyword(s):  
Single Crystal ◽  
Nmr Spectra ◽  
X Ray ◽  
Tert Butyl ◽  
New Compounds ◽  
C Nmr

Ru3(CO)12 reacts with 1-tert-butyl-2,4-cyclopentadiene (1), 1-trimethylsilyl-2,4-cyclopentadiene (2), 1-tert-butyl-3-methyl-2,4-cyclopentadiene (3), 1,3-di(tert-butyl)-2,4-cyclopentadiene (4), 1-iso-propyl-2,3,4,5-tetramethyl-2,4-cyclopentadiene (5), 1-tert-butyl-2,3,4,5-tetramethyl- 2,4-cyclopentadiene (6), 1-phenyl-2,3,4,5-tetramethyl-2,4-cyclopentadiene (7), 2,5- diphenyl-2,4-cyclopentadiene (8), or 2,3,4,5-tetraphenyl-2,4-cyclopentadiene (9) with formation of the corresponding bis[dicarbonyl(cyclopentadienyl) ruthenium(I)] complexes [RuCp# (CO)2]2 1a to 9a. The 1H and 13C NMR spectra of the new compounds 3a and 5a to 9a as well as the single crystal X-ray structures of 1a, 4a, 5a, 7a, 8a, and 9a are reported and discussed

scholarly journals The NMR Spin Systems of Scutellaria 8β,13-Epoxy-neo-clerod-3-en-15,16-olides and Revision of 1H and 13C NMR Spectra Reported Data

2020 ◽  
Vol 15 (10) ◽  
pp. 1934578X2093378
Author(s):  
Josep Coll Toledano
Keyword(s):  
13C Nmr ◽  
Nmr Spectra ◽  
Spin Systems ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Nmr Data ◽  
Reported Data ◽  
New Compounds ◽  
C Nmr ◽  
Shielding Effects

The present review of NMR spectroscopic structural elucidation data of new compounds isolated from Scutellaria species is focused on the title compounds, displaying a peculiar 13-spiro feature. It contains a compilation of 1H and 13C NMR data of these diterpenoids grouped by similar substitution patterns. Comparing shielding effects pointed out not only the identity of some compounds (already reported) but also potential misassignments and convenient revisions to get unambiguous structural proposals.

scholarly journals New Synthetic Routes for 1-Benzyl-1,4,7,10-tetraazacyclododecane and 1,4,7,10-Tetraazacyclododecane-1-acetic Acid Ethyl Ester, Important Starting Materials for Metal-coded DOTA-Based Affinity Tags

2007 ◽  
Vol 62 (3) ◽  
pp. 397-406 ◽  
Author(s):  
Stephan W. Kohl ◽  
Katharina Kuse ◽  
Markus Hummert ◽  
Herbert Schumann ◽  
Clemens Mügge ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Ethyl Ester ◽  
Nmr Spectra ◽  
Acid Ethyl Ester ◽  
Affinity Tags ◽  
X Ray ◽  
H Nmr ◽  
Synthetic Routes ◽  
New Compounds ◽  
C Nmr

Two improved routes to synthesize 1-benzyl-1,4,7,10-tetraazacyclododecane (6) and 1,4,7,10- tetraazacyclododecane-1-acetic acid ethyl ester (11) are described as well as the synthesis of 1-{2-[4-(maleimido-N-propylacetamidobutyl)amino]-2-oxoethyl}-1,4,7,10-tetraazacyclododecane- 4,7,10-triacetic acid (17) and its Y, Ho, Tm, and Lu complexes. The 1H and 13C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of the intermediates 4-benzyl-1,7-bis(p-toluenesulfonyl)diethylenetriamine (3) and 1,4,7-tris(p-toluenesulfonyl)diethylenetriamine (7) are reported and discussed. The rare earth complexes of 17 have been characterized by 1H NMR spectroscopy and MALDI-TOF mass spectrometry.

scholarly journals Synthesis and Characterization of Some New Benzodiazepinium Salt Derivatives under microwave Irradiation

2015 ◽  
Vol 12 (4) ◽  
pp. 753-760
Author(s):  
Baghdad Science Journal
Keyword(s):  
Reaction Mechanism ◽  
Microwave Irradiation ◽  
Benzoic Acid ◽  
Nmr Spectra ◽  
Synthesis And Characterization ◽  
Benzoic Acid Derivatives ◽  
Unexpected Reaction ◽  
Ft Ir ◽  
New Compounds

An attempt to synthesize the benzoimidazol derivatives from the reaction of o-phenylenediamine and benzoic acid derivatives in the presence of ethanol and various ketones under microwave irradiation, 1 , 5 - benzodiazepinum salt derivatives were obtained instead of them. Unexpected reaction was happened for synthesis a new series of benzodiazepinium salt derivatives in a selective yield . The reaction mechanism was also discussed. The new compounds were purified and identified their structures were elucidated using various physical techniques like; FT- IR spectra, micro elemental analysis (C.H.N) and 1H NMR spectra.

N-Benzyl- und N-Heptyl-substituierte Tetraazacyclododecane / N-Benzyl and N-Heptyl Substituted Tetraazacyclodecanes

2004 ◽  
Vol 59 (11-12) ◽  
pp. 1415-1422 ◽  
Author(s):  
Herbert Schumann ◽  
Katharina Kuse ◽  
Sebastian Dechert
Keyword(s):  
Single Crystal ◽  
Mass Spectroscopy ◽  
Copper Complex ◽  
Nmr Spectra ◽  
X Ray ◽  
New Compounds ◽  
C Nmr

1,5-Bis(methylsulfonyloxi)-3-aza-3-p-toluenesulfonylamidopentane (1) reacts with 4-benzyl-1,7- bis(p-toluenesulfonyl)diethylenetriamine (2) and 4-benzyl-1,7-bis(p-nitrophenylsulfonyl)diethylenetriamine (3) and Cs2CO3 yielding 1-benzyl-4,7,10-tris(p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (9a) and 1-benzyl-4,10-bis(p-nitrophenylsulfonyl)-7-p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (10a), respectively. The corresponding dimers 1,13-bis(benzyl)-4,7,10,16,19,22- hexa(p-toluenesulfonyl)-1,4,7,10,13,16,19,22-octaazacyclotetracosane (9b) and 1,13-bis(benzyl)- 4,10,16,22-tetra(p-nitrophenylsulfonyl)-7,19-bis(p-toluenesulfonyl)-1,4,7,10,13,16,19,22-octaazacyclotetracosane (10b) could not be isolated but detected by mass spectroscopy. The reactions of 1 with 4-heptyl-1,7-bis(p-nitrophenylsulfonyl)diethylenetriamine (5) and Cs2CO3 results in the formation of 1-heptyl-4,10-bis(p-nitrophenylsulfonyl)-7-p-toluenesulfonyl)-1,4,7,10-tetraazacyclododecane (11) and 1 reacts with 4-benzyl-diethylenetriamine (4) and Cu(O2CCH3)2 forming the dimeric copper complex [{C6H5CH2N(CH2CH2NH2}2Cu(μ-Cl)OSO2CH3]2 (12). The 1H and 13C NMR spectra of the new compounds as well as the single crystal X-ray structure analyses of 9a, 11, and 12 are reported and discussed.

1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadien-1,2,3,4-tetrayl)tetrakis} ]-(4,1-phenylen)-alkanone und deren Natrium-, Thallium(I)- und Fe(II)-Komplexe / 1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadiene-1,2,3,4-tetrayl)tetrakis} ](4,1 -phenylene)-alkanones and their Sodium, Thallium(I) and Iron(II) Complexes

1993 ◽  
Vol 48 (3) ◽  
pp. 297-312 ◽  
Author(s):  
Herbert Schumann ◽  
Andreas Kucht ◽  
Homa Kucht ◽  
Alexander Lentz ◽  
Lothar Esser ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Sodium Salt ◽  
Nmr Spectra ◽  
Ferrocene Derivatives ◽  
X Ray ◽  
New Compounds ◽  
C Nmr

Tetraphenylcyclopentadiene (1) reacts with acylchlorides RC(O)Cl (R = CH3, C3H7, C5H11,C7H15) to form the corresponding [(cyclopentadiene tetrayl)tetrakis] (4,1-phenylene)alkanones C5H2(C6H4C(O)R-4)4 (2a, 2b, 2c and 2d). 2a reacts with NaNH2 generating the corresponding sodium salt Na[C5H(C6H4C(O)R-4)4] (3a). 2a, 2b, 2c, and 2d react with T1OC2H5 yielding the thallium(I) derivatives Tl[C5H(C6H4C(O)R-4)4] (4a, 4b, 4c, 4d). Octaphenylferrocene (5) reacts with acylchlorides RC(O)Cl (R = CH3, C3H7, C5H11, C7H15) to form octaacylated ferrocenes Fe[C5H(C6H4C(O)R-4)4]2 (6a, 6b, 6c and 6d). 6a can also be prepared by reacting FeI2 with 3a. 6a reacts with NaOBr yielding Fe[C5H(C6H4C(O)OH-4)4]2 (7), which after reaction with C5H11OH and C7H15OH gives the corresponding octaesters Fe[C5H(C6H4C(O)OR-4)4]2 (8c and 8d). 6a and 6b are reduced by N2H4(H2O) to give Fe[C5H(C6H4CH2R-4)4]2 (11a and 11b). The X-ray crystal structures of tetraphenylcyclopentadiene (2 a), as well as of the partially and totally substituted ferrocene derivatives Fe[C5H(C6H4C(O)CH3-4)4][C5H(C6H4C(O)CH3-4)3(C6H5)] (9), Fe[C5H(C6H4C(O)C3H7-4)(C6H5)3]2 (10) and Fe[C5H(C6H4C4H9-4)4]2 (11b) have been determined. The 1H and 13C NMR spectra of the new compounds are reported and discussed.

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