Carbon Suboxide in Preparative Organic Chemistry. New synthetic methods (1)

Kappe, Thomas; Ziegler, E.

doi:10.1002/anie.197404911

Cited by 96 publications

(41 citation statements)

References 111 publications

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“…Inhibition o f the rabbit medula Na/ K-ATPase by the hydrophilic form of the cyclohexameric and macroring closed carbon suboxide, as compared to ouabain. tamn com-(C3O2)n derivatives with preferred "n" values, the here described substances differ essentially from the earlier known, amorphously condensed carbon suboxide polymers (27). The latter compounds have no distinct polymerization degree values and are water-reactive due to the cumulated double bonds preserved at their edges.…”

Section: Resultsmentioning

confidence: 61%

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The Structure of the Digitalislike and Natriuretic Factors Identified As Macrocyclic Derivatives of the Inorganic Carbon Suboxide

Kerek

2000

Hypertens Res

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Section: Resultsmentioning

confidence: 61%

“…The gaseous carbon suboxide 0 = C= C= C= 0 is the doubly dehydrated derivative of malonic acid and in most reactions it gives derivatives of this acid (27). Small amounts of carbon suboxide always accompany carbon monoxide, from which it is easily formed by simple electric discharges.…”

Section: Resultsmentioning

confidence: 99%

The Structure of the Digitalislike and Natriuretic Factors Identified As Macrocyclic Derivatives of the Inorganic Carbon Suboxide

Kerek

2000

Hypertens Res

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“…15,16 Crystallographic studies have also provided direct evidence of energetically and structurally significant interactions between CAO groups and arene rings 9 ; in all these cases the carbonyl group points toward the centroid of the aromatic ring at distances in the range of 2.8 -3.2 Å. Interestingly, the corresponding stabilizing interactions give reason of specific molecular geometries. 9,11 Following our previous studies on the reactivity of carbon suboxide, C 3 O 2 , 17,18 with suitable stabilized phosphorus ylides, which yielded bis-ylidic derivatives of malonic acid, 19 we have obtained new molecules producing self-assembled networks in the solid state.…”

Section: Introductionmentioning

confidence: 98%

Further crystallographic evidence of NH� � �? (system) and CO� � �? (system) interactions: The structures of bis(diarylhydrazonecarbonyl)methylene derivatives [{ArPhC?NNH?C(O)}2CH2] (Ar = Ph, 2-C5H4N, 2-C4H3S)

Ganis¹,

Valle²,

Pandolfo³

et al. 1999

Biopolymers

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“…Although intermediates 3a-d were not isolated in this reaction, they have been previously reported by an Austrian researching group [5].…”

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confidence: 81%

New reactions of carbon suboxide with alkynes

Casu

Bonsignore

Cottiglia

et al. 2003

Journal of Heterocyclic Chem

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Synthesis of 3,4,7,8-tetraalkyl-2-oxa-bicyclo[4.2.0]octa-1(6),3,7-trien-5-ones (4a-d), 4,5,7,8-tetraalkyl-2-oxa-bicyclo[4.2.0]octa-1(6),4,7-trien-3-ones (6a-d) and 3,4,7,8-tetraalkyl-2H,5H-cyclobuta[b]pyrano-[2,3-d]pyran-2,5-diones (7a-d) from the reaction of alkynes (1a-d) with carbon suboxide (2) in various molar ratios is described.J. Heterocyclic Chem., 40, 321 (2003).The reactions of carbon suboxide with different substrates have been extensively studied [1][2][3]. Recently our studies were concentrated on the reactions between carbon suboxide and some alkyne derivatives bearing either a hydroxy or an amino group, to synthesize heterocyclic compounds of potential biological interest [4].In this present paper we wish to report on the synthesis of some new bicyclo and tricyclo derivatives obtained by reacting carbon suboxide and alkynes in three different molar ratios.3,4,7,8-Tetraalkyl-2-oxa-bicyclo[4.2.0]octa-1(6),3,7-trien-5-ones (4a-d) and 4,5,7,8-tetraalkyl-2-oxa-bicyclo-[4.2.0]octa-1(6),4,7-trien-3-ones (6a-d) were obtained by reacting 0.032 mole of alkyne derivatives (1a-d) with 0.016 mole of carbon suboxide (2) in anhydrous chloroform solution. By using this ratio (2:1), yields are about 50%.The proposed reaction mechanism starts from the attack of 1a-d by 2 leading to the 4-oxomethylidene-2-cyclobuten-1-one derivatives (3a-d) followed by the attack of another 1a-d molecule to achieve the compounds (4a-d) and (6a-d). Although intermediates 3a-d were not isolated in this reaction, they have been previously reported by an Austrian researching group [5].Analogously, though in a previous paper we described the structure and stability of similar spiroalkandiones [6], any attempt to isolate 5a-d failed, since they rearranged to form 6a-d (Scheme 1).By reacting compounds 1a-d with 2 in a 1:2 molar ratio, we obtained a gummy product, that was probably a polymer or a macrocycle, along with a small quantity of 4a-d [7]. However, by reacting 1a-d with 2 in a 2:2.5 molar ratio, we obtained the new 3,4,7,8-tetraalkyl-2H,5H-cyclobuta[b]pyrano [2,3-d]pyran-2,5-diones (7a-d), and a

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Carbon Suboxide in Preparative Organic Chemistry. New synthetic methods (1)

Cited by 96 publications

References 111 publications

The Structure of the Digitalislike and Natriuretic Factors Identified As Macrocyclic Derivatives of the Inorganic Carbon Suboxide

The Structure of the Digitalislike and Natriuretic Factors Identified As Macrocyclic Derivatives of the Inorganic Carbon Suboxide

Further crystallographic evidence of NH� � �? (system) and CO� � �? (system) interactions: The structures of bis(diarylhydrazonecarbonyl)methylene derivatives [{ArPhC?NNH?C(O)}2CH2] (Ar = Ph, 2-C5H4N, 2-C4H3S)

New reactions of carbon suboxide with alkynes

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