Highly stereoselective H–D exchange of diastereotopic protons in 4′,1″-dimethyl-1,2,3,4-dibenzylcyclohepta-1,3-diene-6-one

1976 ◽  
Vol 54 (23) ◽  
pp. 3809-3811 ◽  
Author(s):  
Robert R. Fraser ◽  
Philippe J. Champagne
Keyword(s):  
Carbonyl Group ◽  
Title Compound ◽  
Sodium Methoxide ◽  
Rate Ratio

The rates of base-catalyzed H–D exchange of the diastereotopic methylene protons adjacent to the carbonyl group in the title compound have been measured in methanol-O-d. Sodium methoxide as catalyst produced a rate ratio of 73:1. Reasons for the large increase in stereoselectivity over that encountered in the exchange of 4-tert-butylcyclohexanone are proposed.

119Sn, 13C and 1H NMR Spectra of Tris(1-butyl)stannyl D-Glucuronate

1997 ◽  
Vol 62 (8) ◽  
pp. 1169-1176 ◽  
Author(s):  
Antonín Lyčka ◽  
Jaroslav Holeček ◽  
David Micák
Keyword(s):  
Chemical Shift ◽  
Carbonyl Group ◽  
1H Nmr ◽  
Equatorial Plane ◽  
Title Compound ◽  
Nmr Spectra ◽  
Hydroxyl Groups ◽  
Carboxylic Group ◽  
H Nmr ◽  
Oxygen Atoms

The 119Sn, 13C and 1H NMR spectra of tris(1-butyl)stannyl D-glucuronate have been measured in hexadeuteriodimethyl sulfoxide, tetradeuteriomethanol and deuteriochloroform. The chemical shift values have been assigned unambiguously with the help of H,H-COSY, TOCSY, H,C-COSY and 1H-13C HMQC-RELAY. From the analysis of parameters of 119Sn, 13C and 1H NMR spectra of the title compound and their comparison with the corresponding spectra of tris(1-butyl)stannyl acetate and other carboxylates it follows that in solutions of non-coordinating solvents (deuteriochloroform) the title compound is present in the form of more or less isolated individual molecules with pseudotetrahedral environment around the central tin atom and with monodentately bound carboxylic group. The interaction of tin atom with oxygen atoms of carbonyl group and hydroxyl groups of the saccharide residue - if they are present at all - are very weak. In solutions in coordinating solvents (hexadeuteriodimethyl sulfoxide or tetradeuteriomethanol), the title compound forms complexes with one molecule of the solvent. Particles of these complexes have a shape of trigonal bipyramid with the 1-butyl substituents in equatorial plane and the oxygen atoms of monodentate carboxylic group and coordinating solvent in axial positions.

Lithiation of bridgehead positions in 3,6-bridged piperazine-2,5-diones

1982 ◽  
Vol 35 (11) ◽  
pp. 2289 ◽  
Author(s):  
FW Eastwood ◽  
D Gunawardana ◽  
GT Wernert
Keyword(s):  
Carbonyl Group ◽  
Methyl Iodide ◽  
Methyl Ether ◽  
Sodium Methoxide ◽  
Inductive Effect ◽  
Amide Nitrogen

2,5-Dimethyl-2,5 diazabicyclo[2,2,2]octane-3,6-dione can be lithiated at the 1,4 (bridgehead) positions with 2 equiv. of t-butyllithium at -78� and deuterated with D2O (Do, 11.2; Dl, 56.1 ; D2, 30.1%). With butyllithium and methyl iodide the 1,2,5-trimethyl and 1,2,4,5-tetramethyl derivatives are obtained. Treatment of dimethyl 2,6-diaminoheptanedioate dihydrochloride with sodium methoxide in boiling butanol gives 6,8-diazabicyclo[3,2,2]nonane-7,9-dione in 62% yield. N-Methylation of this compound yields 6,8-dimethyl-6,8-diazabicyclo[3,2,2]nonane-7,9-dione which can similarly be lithiated at the 1,5 (bridgehead) positions and deuterated with D2O (Do, 5.6; Dl, 70.8; D2, 23.6%). Lithiation with butyllithium and reaction with methyl iodide, benzyl iodide or bromomethyl methyl ether gives mono-and di-alkylated products at the 1,5-positions. The ability to lithiate the bridgehead positions in these compounds is attributed primarily to a combination of the inductive effect of the carbonyl group and dipole stabilization by the amide nitrogen.

scholarly journals Crystal structure of 1-[(Z)-2-phenylhydrazin-1-ylidene]naphthalen-2(1H)-one

2015 ◽  
Vol 71 (5) ◽  
pp. o303-o303
Author(s):  
Ali Benosmane ◽  
Mohamed Amine Benaouida ◽  
Assia Mili ◽  
Abdelkader Bouchoul ◽  
Hocine Merazig
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Carbonyl Group ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Ring System ◽  
Imino Group ◽  
Compound C ◽  
Supramolecular Chains

In the title compound, C16H12N2O, the dihedral angle between the planes of the benzene ring and naphthalenone ring system is 1.89 (8)°; an intramolecular N—H...O hydrogen bond occurs between the imino group and the carbonyl group. In the crystal, molecules are linked by weak C—H...π interactions into supramolecular chains propagating along the [01-1] direction.

scholarly journals Methyl 2,6-diphenyl-1-p-tolyl-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

2012 ◽  
Vol 68 (8) ◽  
pp. o2392-o2393 ◽  
Author(s):  
K. N. Venugopala ◽  
Susanta K. Nayak ◽  
Bharti Odhav
Keyword(s):  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Title Compound ◽  
Molecular Conformation ◽  
Three Dimensional ◽  
Molecular Assembly ◽  
Boat Conformation ◽  
Π Interactions ◽  
Compound C

In the title compound, C33H32N2O2, the tetrahydropyridine ring adopts a boat conformation with the carbonyl group in ans-cisconformation with respect to the C=C bond of the six-membered tetrahydropyridine ring. The molecular conformation is stabilized by intramolecular N—H...O, C—H...O and C—H...π interactions. Formation of centrosymmetric head-to-head dimers is observed through pairwise intermolecular N—H...O hydrogen bonds. Additional weak C—H...O and C—H...π interactions stabilize the three-dimensional molecular assembly.

scholarly journals (E)-1-(1,3-Benzodioxol-5-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

IUCrData ◽  
2017 ◽  
Vol 2 (1) ◽  
Author(s):  
Karthik Kumara ◽  
S. Naveen ◽  
A. Dileep Kumar ◽  
K. Ajay Kumar ◽  
N. K. Lokanath ◽  
...  
Keyword(s):  
Double Bond ◽  
Carbonyl Group ◽  
Dihedral Angle ◽  
Torsion Angle ◽  
Title Compound ◽  
Compound C ◽  
Benzene Rings ◽  
Olefinic Double Bond

In the title compound, C18H17NO3, the olefinic double bond adopts anEconformation. The molecule is nearly planar as indicated by the dihedral angle of 3.11 (6)° between the benzodioxole and benzene rings. The carbonyl group lies in the plane of the olefinic double bond and the benzodioxole ring. Thetransconformation of the C=C double bond in the central enone group is confirmed by the C=C—C—C torsion angle of −177.82 (14)°.

scholarly journals 2,2,6,6-Tetrabromo-3,4,4,5-tetramethoxycyclohexanone

2014 ◽  
Vol 70 (7) ◽  
pp. o826-o826
Author(s):  
Md. Serajul Haque Faizi ◽  
Ashraf Mashrai ◽  
M. Shahid
Keyword(s):  
Hydrogen Bonding ◽  
Schiff Base ◽  
Carbonyl Group ◽  
Title Compound ◽  
Chair Conformation ◽  
Molecular Bromine ◽  
Axis Direction ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Methoxy Groups

In the title compound, C10H14Br4O5, synthesized from the methoxy Schiff baseN-(pyridin-2-ylmethyl)methoxyaniline and molecular bromine, the cyclohexanone ring has a chair conformation with one of the four methoxy groups equatorially orientated with respect to the carbonyl group and the others axially orientated. The C—Br bond lengthsvary from 1.942 (4) to1.964 (4) Å. In the crystal, weak C—H...Ocarbonylhydrogen-bonding interactions generate chains extending along theb-axis direction. Also present in the structure are two short intermolecular Br...Omethoxyinteractions [3.020 (3) and 3.073 (4) Å].

scholarly journals 1,5-Bis(4-chlorophenyl)penta-1,4-dien-3-one

2006 ◽  
Vol 62 (5) ◽  
pp. o1973-o1975 ◽  
Author(s):  
Ray J. Butcher ◽  
H. S. Yathirajan ◽  
B. K. Sarojini ◽  
B. Narayana ◽  
K. K. Vijaya Raj
Keyword(s):  
Carbonyl Group ◽  
Optical Activity ◽  
Title Compound ◽  
Rotation Axis ◽  
Compound C ◽  
Non Linear ◽  
Linear Optical

The title compound, C17H12Cl2O, shows significant non-linear optical activity. A twofold rotation axis passes through the carbonyl group.

scholarly journals Methyl 4-amino-2-chloropyrimidine-5-carboxylate

2014 ◽  
Vol 70 (8) ◽  
pp. o869-o869
Author(s):  
Ya-Ming Wu
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Carbonyl Group ◽  
Title Compound ◽  
Maximum Deviation ◽  
Amino Group ◽  
Compound C ◽  
Supramolecular Chains

In the title compound, C6H6ClN3O2, all non-H atoms are approximately coplanar [maximum deviation = 0.012 (4) Å]; an intramolecular N—H...O hydrogen bond occurs between the amino group and the carbonyl group. In the crystal, molecules are linked by N—H...N hydrogen bonds into supramolecular chains propagated along [101].

2-(Cyclopentylsulfanyl)-6-(1-naphthoyl)pyrimidin-4(3H)-one

2006 ◽  
Vol 62 (4) ◽  
pp. o1485-o1487
Author(s):  
Lei Ji ◽  
Yun-Yan Kuang ◽  
Fen-Er Chen ◽  
Min-Qin Chen
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Carbonyl Group ◽  
Title Compound ◽  
Ring System ◽  
Compound C ◽  
Naphthyl Ring

In the structure of the title compound, C20H18N2O2S, the carbonyl group, the naphthyl ring system and the cyclopentyl ring are not in the plane of the pyrimidinyl ring. In the crystal structure, pairs of molecules are connected into dimers via N—H...O hydrogen bonding

(aR,1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (4-tert-butylcyclohexylidene)acetate

2006 ◽  
Vol 62 (7) ◽  
pp. o2967-o2968
Author(s):  
Jin-Long Wu
Keyword(s):  
Carbonyl Group ◽  
Title Compound ◽  
Olefinic Bond ◽  
Compound C

In the molecule of the title compound, C28H42O2, the two cyclohexane rings adopt chair conformations. The olefinic bond and carbonyl group are approximately coplanar.

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