Neryl- and geranyltriethylammonium halides in the allylation of sodium diethyl malonate. The effect of the leaving group of the allylating reagent on the selectivity of the reaction

1994 ◽  
Vol 43 (2) ◽  
pp. 249-251 ◽  
Author(s):  
E. A. Petrushkina ◽  
L. I. Zakharkin
Keyword(s):  
Diethyl Malonate ◽  
Leaving Group ◽  
Sodium Diethyl Malonate

Diethyl malonate as leaving group: Facile synthesis of some 1,3,4-benzotriazepines and benzotriazepinones

1969 ◽  
Vol 47 (3) ◽  
pp. 489-494 ◽  
Author(s):  
C. Podesva ◽  
G. Kohan ◽  
K. Vagi
Keyword(s):  
Double Bond ◽  
Hydrazine Hydrate ◽  
Diethyl Malonate ◽  
Facile Synthesis ◽  
Leaving Group ◽  
Diethyl Ethoxymethylenemalonate ◽  
Bond Isomers

Reaction between 2-(2′,2′-bis-carboethoxyvinylamino)-benzophenones, resulting from the condensation of 2-aminobenzophenones with diethyl ethoxymethylenemalonate, and hydrazine hydrate yields 5-hydroxy-5-phenyl-1,3,4-3H-4,5-dihydrobenzotriazepines or their double bond isomers. These products on acetylation afford O,N,N-triacetates, which on treatment with ammonia are transformed into 4-phenylquinazolines. Structure proof of these substances is reported.

scholarly journals On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

2020 ◽  
Vol 16 ◽  
pp. 1863-1868
Author(s):  
Ilya V Taydakov ◽  
Mikhail A Kiskin
Keyword(s):  
Acetic Acid ◽  
Malonic Acid ◽  
Diethyl Malonate ◽  
Toxic Substances ◽  
New Approach ◽  
Preparative Yield ◽  
Benzyl Halides ◽  
Acidic Conditions ◽  
Hydrolysis Of ◽  
Sodium Diethyl Malonate

Diethyl 2-(perfluorophenyl)malonate was synthesized in 47% isolated yield by the reaction of sodium diethyl malonate and hexafluorobenzene. The resulting compound was considered as a starting material for synthesizing 2-(perfluorophenyl)malonic acid by hydrolysis. It was found that the desired 2-(perfluorophenyl)malonic acid could not be obtained from this ester by hydrolysis, neither under basic nor under acidic conditions. Nevertheless, hydrolysis of the ester with a mixture of HBr and AcOH gave 2-(perfluorophenyl)acetic acid in a good preparative yield of 63%. A significant advantage of this new approach to 2-(perfluorophenyl)acetic acid is that handling toxic substances such as cyanides and perfluorinated benzyl halides is avoided.

ChemInform Abstract: Reactions of Sodium Diethyl Malonate with Functionalized 2,3-Dichlorocyclopentenones. Preparation of Water-Soluble Derivatives.

ChemInform ◽  
2010 ◽  
Vol 30 (50) ◽  
pp. no-no
Author(s):  
N. A. Ivanova ◽  
A. M. Shainurova ◽  
R. R. Akhmetvaleev ◽  
T. A. Belogaeva ◽  
M. S. Miftakhov
Keyword(s):  
Diethyl Malonate ◽  
Water Soluble ◽  
Sodium Diethyl Malonate

Preparation and absolute configuration at C(20) of 21-nor-5α-cholan-24→20-olide derivatives

1981 ◽  
Vol 46 (1) ◽  
pp. 107-117 ◽  
Author(s):  
Vladimír Pouzar ◽  
Miroslav Havel
Keyword(s):  
Acetic Acid ◽  
Absolute Configuration ◽  
Nmr Spectra ◽  
Lithium Salt ◽  
Diethyl Malonate ◽  
Methyl Propionate ◽  
H Nmr ◽  
Sodium Diethyl Malonate

The lactones X and XI were obtained on reaction of the aldehyde III with lithium salt of methyl propionate followed by hydrogenation of the intermediary esters IV and V. Treatment of the epoxides XXI and XXII with dilithium salt of acetic acid yielded the lactones X and XI. These lactones were also obtained by reaction of the epoxides XXI and XXII with sodium diethyl malonate through intermediates XXIII and XXV. The preparation of α-methylene lactones XXVII and XXVIII is also described. The 20R configuration was established for the lactones X, XXIII and XXVII while the lactones XI, XXV and XXVIII were assigned the 20S configuration both on the basis of 1H-NMR spectra and chemical correlations.

Rearrangement of a Vinylallylammonium Salt Effected by Sodium Diethyl Malonate

2004 ◽  
Vol 74 (1) ◽  
pp. 144-145 ◽  
Author(s):  
S. T. Kocharyan ◽  
V. S. Ovsepyan ◽  
A. V. Babakhanyan ◽  
V. E. Karapetyan ◽  
G. A. Panosyan
Keyword(s):  
Diethyl Malonate ◽  
Sodium Diethyl Malonate

General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

2018 ◽  
Author(s):  
Marc Montesinos-Magraner ◽  
Matteo Costantini ◽  
Rodrigo Ramirez-Contreras ◽  
Michael E. Muratore ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Chemical Space ◽  
Synthetic Approach ◽  
Asymmetric Cyclopropanation ◽  
Redox Active ◽  
Wide Range ◽  
Leaving Group ◽  
Stereoelectronic Properties ◽  
Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

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