Comparison of 13C and 1H N-alkyl shifts of isomeric alkyl tetrazoles: some ambident benzylations

1977 ◽  
Vol 55 (9) ◽  
pp. 1564-1566 ◽  
Author(s):  
R. N. Butler ◽  
T. M. McEvoy ◽  
F. L. Scott ◽  
J. C. Tobin
Keyword(s):  
Alkyl Group ◽  
Structural Units ◽  
Structural Assignment ◽  
Derivatives Of ◽  
C Nmr

13C nmr alkyl shifts of N-alkyl tetrazoles and azoles follow the pattern of proton shifts. The shielding of the N-alkyl group increases for the structural units[Formula: see text]The carbon spectra are more reliable for structural assignment. Syntheses of a number of mono- and dibenzyl derivatives of benzaldehyde tetrazol-5-ylhydrazone are reported.

Thermal cyclocondensations of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino derivatives of 2-propenoic acid

1987 ◽  
Vol 52 (12) ◽  
pp. 2918-2925 ◽  
Author(s):  
Viktor Milata ◽  
Dušan Ilavský
Keyword(s):  
Uv Spectra ◽  
Propenoic Acid ◽  
Amino Derivatives ◽  
Derivatives Of ◽  
C Nmr ◽  
Ir And Uv Spectra

The cyclization of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino-2-cyano- and 2-ethoxycarbonyl-2-propenoate esters Ia, b-IVa, b under the conditions of the Gould-Jacobs reaction leads to angularly ring-fused substituted imidazo or triazolo[4,5-f] (V, VI) and [4,5-h] (VII, VIII) quinolines, respectively. The esters Vb-VIIIb have been transformed into the corresponding chloroderivatives Vc-VIIIc. 3-N(5-Benzimidazolyl and 5-benztriazolyl)amino-2-cyano-2-propenenitriles are cyclized in the presence of aluminium(III) chloride to give the aminoquinolines Vd, VId. The structure of the products has been characterized by their 1H, 13C NMR, IR, and UV spectra.

Preparation of 2,3-Dideoxy-2,3-epimino and 3,4-Dideoxy-3,4-epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses by Mitsunobu Reaction

1998 ◽  
Vol 63 (6) ◽  
pp. 813-825 ◽  
Author(s):  
Jiří Kroutil ◽  
Tomáš Trnka ◽  
Miloš Buděšínský ◽  
Miloslav Černý
Keyword(s):  
Nmr Spectra ◽  
Mitsunobu Reaction ◽  
Derivatives Of ◽  
C Nmr

A series of new 2-, 3- and 4-benzylamino-2-, 3- and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses by treatment with benzylamine and converted into 2,3-(N-benzylepimino)-2,3-dideoxy- and 3,4-(N-benzylepimino)-3,4-dideoxy-β-D-hexopyranoses of the D-allo, D-galacto and D-talo configuration by Mitsunobu reaction. The structures of benzylamino and benzylimino derivatives were confirmed by 1H and 13C NMR spectra.

Triazene derivatives of (1,x-)diazacycloalkanes. Part VI. 3-({5,5-Dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines — Synthesis, characterization, and X-ray crystal structure

2006 ◽  
Vol 84 (10) ◽  
pp. 1294-1300 ◽  
Author(s):  
Keith Vaughan ◽  
Shasta Lee Moser ◽  
Reid Tingley ◽  
M Brad Peori ◽  
Valerio Bertolasi
Keyword(s):  
Crystal Structure ◽  
Significant Degree ◽  
Ion Trapping ◽  
Published Data ◽  
X Ray ◽  
X Ray Crystallography ◽  
Diazonium Ion ◽  
Derivatives Of ◽  
C Nmr

Reaction of a series of diazonium salts with a mixture of formaldehyde and 1,2-diamino-2-methylpropane affords the 3-({5,5-dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines (1a–1f) in excellent yield. The products have been characterized by IR and NMR spectroscopic analysis, elemental analysis, and X-ray crystallography. The X-ray crystal structure of the p-methoxycarbonyl derivative (1c) establishes without question the connectivity of these novel molecules, which can be described as linear bicyclic oligomers with two imidazolidinyl groups linked together by a one-carbon spacer. This is indeed a rare molecular building block. The molecular structure is corroborated by 1H and 13C NMR data, which correlates with the previously published data of compounds of types 5 and 6 derived from 1,3-propanediamine. The triazene moieties in the crystal of 1c display significant π conjugation, which gives the N—N bond a significant degree of double-bond character. This in turn causes restricted rotation around the N—N bond, which leads to considerable broadening of signals in both the 1H and 13C NMR spectra. The molecular ion of the p-cyanophenyl derivative (1b) was observed using electrospray mass spectrometry (ES + Na). The mechanism of formation of molecules of type 1 is proposed to involve diazonium ion trapping of the previously unreported bisimidazolidinyl methane (13).Key words: triazene, bistriazene, imidazolidine, synthesis, X-ray crystallography, NMR spectroscopy.

4-N-Benzazolylamino Derivatives of 3-Y-3-Buten-2-one

1992 ◽  
Vol 57 (3) ◽  
pp. 531-539 ◽  
Author(s):  
Viktor Milata ◽  
Dušan Ilavský ◽  
Igor Goljer ◽  
Ján Leško
Keyword(s):  
Nucleophilic Substitution ◽  
Mass Spectra ◽  
Spectral Measurements ◽  
Mild Conditions ◽  
Derivatives Of ◽  
C Nmr

Ethoxymethylene derivatives of 2,4-pentanedione (Ia), 3-oxobutanenitrile (Ib), methyl (Ic) or ethyl (Id) 3-oxobutanoate give with 4- or 5-aminobenzimidazole or benzotriazole, respectively, under mild conditions products of nucleophilic substitution II-V. Structure of these compounds was discussed on the basis of their spectral measurements - IR, UV, 1H, 13C NMR and mass spectra.

β-Hydroxydithiozimtsäurederivate als Liganden. Synthese und Charakterisierung neuartiger 1,1-Ethendithiolato- und O,S-Chelatkomplexe / Derivatives of β -Hydroxydithiocinnamic Acids as Ligands. Syntheses and Characterisation of Novel 1,1-Ethenedithiolato and O,S-Chelate Complexes

2007 ◽  
Vol 62 (3) ◽  
pp. 475-482 ◽  
Author(s):  
Karsten Schubert ◽  
Helmar Görls ◽  
Wolfgang Weigand
Keyword(s):  
Bidentate Ligand ◽  
Molecular Structures ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
X Ray ◽  
H Nmr ◽  
Hexyl Ester ◽  
Elemental Analyses ◽  
Derivatives Of ◽  
C Nmr

Starting from 4-bromoacetophenone 1, the 4-bromo-β -hydroxydithiocinnamic acid 2 and the 4-bromo-β -hydroxydithiocinnamic acid hexyl ester 3 were prepared using carbon disulfide and potassium-tert-butylate as a base. Acting as a ligand, the acid gives 1,1-ethenedithiolato complexes with (Ph3P)2Pt(II) (4a), (Et3P)2Pt(II) (4b), dppePt(II) (4c), (Ph3P)2Pd(II) (4d), dppePd(II) (4e), and dppeNi(II) (4f). In contrast to the acid, the deprotonated ester 3 forms a monoanionic bidentate ligand. [O,S] Complexes of Pt(II) (5a), Pd(II) (5b) and Ni(II) (5c) were obtained. All complexes have been fully characterised using 1H NMR, 13C NMR and 31P NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analyses. The molecular structures of the complexes 4b and 5a - 5c were determined by X-ray diffraction analyses.

Synthese von Derivaten des 1-Adamantylbenzols /Synthesis of Derivatives of 1-Adamantylbenzene

1979 ◽  
Vol 34 (9) ◽  
pp. 1286-1288 ◽  
Author(s):  
Jörn-Volker WeiB ◽  
Victor Wray ◽  
Reinhard Schmutzler
Keyword(s):  
Nmr Spectroscopy ◽  
Lewis Acid ◽  
Type Reaction ◽  
Benzene Toluene ◽  
Derivatives Of ◽  
C Nmr

Abstractp-Di(1-adamantyl)benzene (6a), a mixture of the m- and p-isomers of 1-adamantyl-toluene (6b), and p-(l-adamantyl)bromobenzene (6c) were obtained in a Friedel-Crafts type reaction from 1-adamantyl fluoride and benzene, toluene, bromobenzene, respectively, in the presence of the Lewis acid phenyltetrafluorophosphorane. Characterisation of the products -all previously described in the literature -was by analysis and 13C NMR spectroscopy.

Conformation of ring A in triterpenoid ketones. Carbon-13 chemical shifts and spin-lattice relaxation times of lupane and 18α-oleanane derivatives

1989 ◽  
Vol 54 (7) ◽  
pp. 1928-1939 ◽  
Author(s):  
Miloš Buděšínský ◽  
Jiří Klinot
Keyword(s):  
Chemical Shifts ◽  
Relaxation Times ◽  
Lattice Relaxation ◽  
Chair Conformation ◽  
Spin Lattice Relaxation ◽  
Spin Lattice ◽  
Structural Assignment ◽  
Boat Form ◽  
The One ◽  
C Nmr

13C NMR spectra of sixteen lupane and 19β,28-epoxy-18α-oleanane triterpenoids I-XVI were measured and a complete structural assignment of chemical shifts was made. For most compounds also the carbon spin-lattice relaxation times T1 were obtained. Characteristic differences in chemical shifts of some carbon atom signals were found between 2α-methyl-3-oxo and 2α-methyl-1-oxo derivatives II, V and VIII with chair conformation of the ring A on the one hand and their 2β-isomers III, VI and IX (boat form) on the other. Using these 2-methyl ketones as models, the chair-boat population in allobetulone (I), 3-oxo-28-lupanenitrile (IV) and 1-oxo derivative VII was determined. The results agree well with the data obtained by other physical methods.

Synthesis, spectroscopic characterization and structural studies of organotin monothiocarbonates. Crystal structures of Ph3Sn[SCO2Me] and Ph3Sn[SCO2(i-Pr)]

2000 ◽  
Vol 78 (9) ◽  
pp. 1214-1221 ◽  
Author(s):  
John E Drake ◽  
Jincai Yang
Keyword(s):  
Intramolecular Interaction ◽  
Spectroscopic Characterization ◽  
Triclinic Space Group ◽  
Cell Parameters ◽  
X Ray Crystallography ◽  
H Nmr ◽  
Trigonal Bipyramidal ◽  
Considerable Distortion ◽  
Derivatives Of ◽  
C Nmr

O-alkyl monothiocarbonate (monoxanthate) derivatives of tin were obtained by the reaction of a sodium salt of the monothiocarbonic acid with an organotin chloride to give Ph3Sn[SCO2R], Ph2Sn[SCO2R]2, and Me3Sn[SCO2R], where R = Me and i-Pr. The compounds have been characterized by infrared, Raman, 1H NMR, and 13C NMR spectroscopy, as well as mass spectrometry, and in two cases by X-ray crystallography. Ph3Sn[SCO2Me] (1) and Ph3Sn[SCO2(i-Pr)] (2), crystallize in the triclinic space group P[Formula: see text] (no. 2) with cell parameters a = 10.218(4), b = 10.568(6), c = 9.366(7) Å, α = 106.73(5), β = 96.99(5), γ = 85.55(4)°, V = 960(1) Å3, and Z = 2 for 1; and a = 14.793(2), b = 17.856(3), c = 9.813(3) Å, α = 103.86(5), β = 98.36(5), γ = 106.85(4)°, V = 2343(1) Å3, and Z = 2 for 2. The latter has two molecules in the asymmetric unit. The immediate environment about tin in both 1 and 2 is that of the expected distorted tetrahedron. However, the orientation of the monothiocarbonate group is such that there is an Sn-O intramolecular interaction of 3.040(8) for 1 and 3.05(2) Å on average for 2. Thus, the considerable distortion is consistent with a tendency to form a five-coordinate, trigonal bipyramidal species with one of the O-Sn-C angles approaching 180o (153.4(4) for 1 and an average of 157.1(6) for 2). Estimations of the Pauling partial bond orders suggest this weak Sn-O interaction is slightly stronger than the corresponding Ge-O interaction in the analogous germanium derivative, Ph3Ge[SCO2Me].Key words: structure, tin, methyl, phenyl, isopropyl, monothiocarbonates.

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