(Z)- and (E)-3-Alkyldine-1,3-dihydroindol-2-ones : influence of configuration on the transmission of the inductive effect to the carbonyl group

1976 ◽  
pp. 150 ◽  
Author(s):  
Gianfranco Tacconi ◽  
Lucia Dacrema Maggi ◽  
Pierpaolo Righetti ◽  
Giovanni Desimoni ◽  
Ornella Azzolina ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Inductive Effect

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.

ChemInform Abstract: (Z)- AND (E)-3-ALKYLIDENE-1,3-DIHYDROINDOL-2-ONES. INFLUENCE OF CONFIGURATION ON THE TRANSMISSION OF THE INDUCTIVE EFFECT TO THE CARBONYL GROUP

1976 ◽  
Vol 7 (14) ◽  
pp. no-no
Author(s):  
GIANFRANCO TACCONI ◽  
LUCIA DACREMA MAGGI ◽  
PIERPAOLO RIGHETTI ◽  
GIOVANNI DESIMONI ◽  
ORNELLA AZZOLINA ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Inductive Effect

Ultraviolet photoelectron spectra of 2-norbornanone, 2,5-norbornanedione, their alkyl derivatives and thio-analogues. An investigation of transannular interactions by photoelectron spectroscopy

1980 ◽  
Vol 58 (16) ◽  
pp. 1659-1665 ◽  
Author(s):  
David C. Frost ◽  
Nicholas P. C. Westwood ◽  
Nick H. Werstiuk
Keyword(s):  
Carbonyl Group ◽  
Photoelectron Spectroscopy ◽  
Inductive Effect ◽  
Photoelectron Spectra ◽  
Methyl Substitution ◽  
Bond Interaction ◽  
Alkyl Derivatives ◽  
Semi Empirical ◽  
Small Separation

HeI photoelectron spectra are reported for a series of methyl-substituted monoketones and diketones based on 2-norbornanone. The effect of methyl substitution, and the inductive effect of a second carbonyl group has been studied. The diketones show a small separation between the two ketone moieties due to a through-bond interaction. Replacement with a thiocarbonyl group permits a comparison of the relative C=S and C=O interactions. The relative merits of the semi-empirical HAM/3 and CNDO/2 methods for such molecules are assessed.

Photoelectron spectrum of tropone. Inductive effect of carbonyl group

1974 ◽  
Vol 96 (6) ◽  
pp. 1952-1954 ◽  
Author(s):  
J. C. Buenzli ◽  
D. C. Frost ◽  
Larry Weiler
Keyword(s):  
Carbonyl Group ◽  
Photoelectron Spectrum ◽  
Inductive Effect

Transfer of inductive effect in thiophene series

1976 ◽  
Vol 41 (5) ◽  
pp. 1541-1550 ◽  
Author(s):  
M. Janda ◽  
J. Šrogl ◽  
M. Němec ◽  
K. Kalfus
Keyword(s):  
Inductive Effect ◽  
Thiophene Series

Polarographic reduction of α-(4-ethylbenzoyl)-α,β-dibromopropionic acid on mercury dropping electrode

1979 ◽  
Vol 44 (4) ◽  
pp. 1318-1323
Author(s):  
Miloslava Počtová
Keyword(s):  
Electrochemical Reduction ◽  
Carbonyl Group ◽  
Polarographic Reduction ◽  
Polarographic Wave ◽  
Intermediate Products ◽  
Active Intermediate

A mechanism of the electrochemical reduction of β-(4-ethylbenzoyl)-α,β-dibromopropionic acid is suggested based on the results of classical polarography and polarography with Kalousek's switch and on the identification of the polarographically active intermediate products. The substance converts to β-4-ethylbenzoylacrylic acid on the electrochemical elimination of the bromine atoms, and the latter acid is reduced further to β-4-ethylbenzoylpropionic acid. The most negative polarographic wave corresponds to the reduction of the carbonyl group in the benzoyl part of the last acid.

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