Stereochemistry of acyl halide addition to olefins. Intramolecular cyclization of cis-4-cyclooctene-1-carboxylic acid chloride

1968 ◽  
Vol 33 (4) ◽  
pp. 1545-1550 ◽  
Author(s):  
William F. Erman ◽  
Herbert C. Kretschmar
Keyword(s):  
Carboxylic Acid ◽  
Intramolecular Cyclization ◽  
Acid Chloride ◽  
Acyl Halide ◽  
Carboxylic Acid Chloride

The dimethyl formamide – acyl halide complex and its application to the synthesis of acyl azides

1967 ◽  
Vol 45 (11) ◽  
pp. 1247-1251 ◽  
Author(s):  
Donald E. Horning ◽  
Joseph M. Muchowski
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Direct Conversion ◽  
Dimethyl Formamide ◽  
Acid Salt ◽  
Acyl Halide ◽  
Acyl Azides ◽  
Selective Formation ◽  
Carboxylic Acid Salt ◽  
Acid Azide

A description of the conditions which favor the formation of the acid chloride – dimethyl formamide complex is given. The utility of the complex is illustrated by its application to the synthesis of acyl azides and, in particular, by the selective formation of 3-bromopropionyl azide from the corresponding acid chloride. The complex also results from a carboxylic acid salt and N,N-dimethyl chloroformiminium chloride, and thus provides an alternative method of effecting the direct conversion of a carboxylic acid into the corresponding acid azide.

Synthesis of amino acid diazoketones

1986 ◽  
Vol 64 (11) ◽  
pp. 2097-2102 ◽  
Author(s):  
George R. Pettit ◽  
Paul S. Nelson
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Acid Chloride ◽  
Low Temperatures ◽  
Oxalyl Chloride ◽  
Acyl Chloride ◽  
Carboxyl Group ◽  
Carboxylic Acid Chloride ◽  
Active Esters ◽  
Active Ester

A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt–Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide–tetrahydrofuran followed by diazomethane at −23 °C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23–26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

Synthesis and Reactions of Some 1H-Pyrazole-3 Carboxylic Acid Chloride

2009 ◽  
Vol 15 (4) ◽  
Author(s):  
İhan Özer İlhan ◽  
Sevgi Zühal ◽  
Zülbiye Önal ◽  
Emin Saripinar
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Carboxylic Acid Chloride

scholarly journals Crystal structures of 1′-aminocobaltocenium-1-carboxylic acid chloride monohydrate and of its azo dye 1′-[2-(1-amino-2,6-dimethylphenyl)diazen-1-yl]cobaltocenium-1-carboxylic acid hexafluoridophosphate monohydrate

2019 ◽  
Vol 75 (2) ◽  
pp. 208-213 ◽  
Author(s):  
Markus Jochriem ◽  
Klaus Wurst ◽  
Holger Kopacka ◽  
Benno Bildstein
Keyword(s):  
Carboxylic Acid ◽  
Water Molecule ◽  
Functional Groups ◽  
Acid Chloride ◽  
Supramolecular Network ◽  
Carboxylic Acid Chloride ◽  
Positional Disorder ◽  
Counter Ion ◽  
Chloride Monohydrate ◽  
Hydrogen Bonded

1′-Aminocobaltocenium-1-carboxylic acid chloride, [Co(C5H6N)(C6H5O2)]Cl·H2O, (3), and its azo derivative 1′-[2-(1-amino-2,6-dimethylphenyl)diazen-1-yl]cobaltocenium-1-carboxylic acid hexafluoridophosphate, [Co(C13H14N3)(C6H5O2)]PF6·H2O (5) were obtained from cobaltocenium-1,1′-dicarboxylic acid hexafluoridophosphate by converting one carboxyl group to its chlorocarboxyl derivative followed by chloride/azide exchange, Curtius rearrangement, diazotiation and azo coupling with 2,6-dimethylaniline. Both title compounds crystallize as their monohydrates. In the crystal structure of 3, both functional groups lie in the same direction, with the Cp rings being nearly eclipsed, and participate in an extended hydrogen-bonded supramolecular network including the counter-ion and the water molecule of crystallization. Although the functional groups in 5 are somewhat further apart, bearing a greater torsion angle with the Cp rings now staggered, a similar supramolecular network is observed with not only the carboxylic acid and azo groups, but also with the more remote amino group participating in a hydrogen-bonded network, again including the counter-ion and the water molecule. The hexafluoridophosphate ion shows positional disorder. Compound 3 was refined as an inversion twin. In 5, each of the six F atoms is disordered over two sets of sites in a 1:1 ratio.

ChemInform Abstract: REACTIONS OF 2-PHENYL-4-CHLOROQUINOLINE-3-CARBOXYLIC ACID CHLORIDE

1975 ◽  
Vol 6 (12) ◽  
pp. no-no
Author(s):  
WANDA ZANKOWSKA-JASINSKA ◽  
MARIAN BALA ◽  
JAN BOKSA
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Carboxylic Acid Chloride
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