Struktur und Reaktionen des Hydrindantins und einiger seiner Derivate

Regitz, Manfred; Schwall, Horst; Heck, Gerhard; Eistert, Bernd; Bock, Gustav

doi:10.1002/jlac.19656900110

Cited by 40 publications

(14 citation statements)

References 20 publications

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“…For comparison purposes we reacted as well bis[bis(trimethylsilyl)amino]germanium(II) and -tin(II) with 2-diazo-1,3-indanedione according to eq 5, thus obtaining the corresponding indeno[2,1- e ]-1,3,4,2-oxadiazametallanin-5( 2H )-ones 7 and 8 . Besides 7 also a dimeric compound ( 7 ) 2 crystallized at −25 °C forming an olive solid; by different crystallization procedures, crystals of monomeric (yellow) and dimeric (green) 7 could be separated.…”

Section: Resultsmentioning

confidence: 99%

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Products of the Reactions of 2-Diazomalonate and of 2-Diazoindanedione with Germylenes and Stannylenes

et al. 1996

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Products obtained in the reaction between germylenes or stannylenes with dimethyl 2-diazomalonate and 2-diazo-1,3-indanedione have been isolated and characterized. Compounds thus prepared are the 2H-1,3,4,2-oxadiazagermanine-5-carboxylates 1 and 2, the indeno[2,1-e]-1,3,4,2-oxadiazametallanin-5(2H)-ones 7 and 8, the 6-oxa-3,4-diaza-2,7digermabicyclo[3.2.0]hept-3-ene-carboxylate 3, resulting from the thermal treatment of 2, and the unsymmetrical dimer of 7, (7) 2 . Furthermore the reaction products of 2 with t-BuNCO, 4, with PhCHO, 5, and with H 2 CdCHCHO, 6, and compound 9 obtained by partial hydrolysis of 7 and (7) 2 were isolated. The compounds were characterized by NMR spectroscopy ( 1 H, 13 C, and 29 Si and in part 15 N and 119 Sn), MS (EI or FI), and elemental analyses. X-ray crystal structure determinations are presented for 1, 2, 3, 4, and (7) 2 .

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Section: Resultsmentioning

confidence: 99%

“…Starting materials were prepared according to the following references: [(2,6- i Pr 2 C 6 H 3 )(Me 3 Si)N] 2 Ge, [(Me 3 Si) 2 N] 2 Ge, [(Me 3 Si) 2 N] 2 Sn, N 2 C(COOMe) 2 , N 2 C(CO) 2 C 6 H 4 …”

Section: Methodsmentioning

confidence: 99%

Products of the Reactions of 2-Diazomalonate and of 2-Diazoindanedione with Germylenes and Stannylenes

et al. 1996

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“…5-Bromo-2,2-dimethoxyindane-1,3-dione (13) was prepared from phthalic acid according to published procedures. 13,14 Aromatic Nucleophilic Displacement of 5-Bromo-2,2-dimethoxyindane-1,3-dione (13); General Procedure…”

Section: Methodsmentioning

confidence: 99%

“…H NMR (CDCl 3 /TMS): δ = 2.50 (s, 3 H), 3.60 (s, 6 H), 7.70-7.85 (m, 3 H) 13. C NMR (CDCl 3 /TMS): δ = 6.8, 51.7, 91.1, 122.0, 123.9, 136.5, 136.6, 139.5, 147.0, 192.6, 193.3.…”

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confidence: 99%

Synthesis of Fingerprint Reagents: Aromatic Nucleophilic Substitution as a Route to 5-Substituted Ninhydrins

Della¹,

Janowski²,

Pigou³

et al. 1999

Synthesis

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An efficient synthesis of 5-substituted 2,2-dimethoxy-1,3-indanediones by nucleophilic displacement of the parent 5-bromo derivative by oxygen, sulfur and selenium-based nucleophiles has been developed. Mild acid hydrolysis of the ketals enables their smooth conversion into the corresponding ninhydrins, which are potential fingerprint reagents.Despite the continuing search for alternative reagents for the development of latent fingerprints on paper, none has been found with sufficient advantages in performance and cost to supplant ninhydrin (1). Thus, while there are some drawbacks associated with the use of 1, 1-4 it is superior in terms of its combined reactivity, solubility, ease of detection, and economy. The development of the print relies upon the reaction of the ninhydrin with α-amino acid residues adhering to the paper to give a deeply colored product 2 known as Ruhemann's purple 5 and, over the years, considerable effort has been directed to the synthesis of ninhydrin analogues 6 and related compounds. 7 In a more recent development, the visualization of weakly developed prints can be enhanced by utilizing the fluorogenic properties of Ruhemann's purple when complexed with zinc(II) or cadmium(II) salts. 2,8 In view of the observation 4,9 that the complex derived from 5-methoxyninhydrin (3) has been found to possess fluorogenic properties superior to those of the product from 1, it has been suggested 9 that the modified ninhydrin most likely to produce enhanced prints is that with substitution at the C-5 position rather than at C-4. In this context, it is noteworthy that sulfur-containing ninhydrins such as 5-methylthioninhydrin (4) have recently been claimed 10 to surpass both 1 or 3 as a fingerprint reagent. Syntheses of 4 have recently been reported. 10,11 The preparation of the related species, thianinhydrin 5, has recently been described 6 and shown to be as effective as ninhydrin. Considering the favorable properties conferred by the methoxy and methylthio groups upon the Ruhemann's purple complex derived from ninhydrin (1), we felt it important to probe whether such activity could be further enhanced by the next Group VI member, the selenium-based ninhydrin 6. The preparation of 5-methylselenoninhydrin (6) was, therefore, the primary goal of this work. An additional aim, however, was to develop alternative, readily achievable, efficient and economical strategies to the synthesis of analogs of 4 and 6, such as their aryl derivatives 7 and 8. Furthermore, we were conscious of the fact that the type of chlorofluorocarbon solvents that have been commonly employed in the protocols involving development of fingerprints over many years are in the process of being phased out worldwide. It was therefore considered essential to prepare ninhydrins which have increased solubility in hydrocarbon solvents, the likely replacements for the freons. Accordingly, a further goal was the synthesis of the aryl ether 9 together with other ethers, as well as the 5-alkoxy-, 5-alkylthio-and 5-alkylseleno derivatives of ninh...

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“…The reaction of diazoalkanes with thiocarbonyl compounds has been extensively studied (1)(2)(3)(4)(5), and d~verse products, the nature of which depends on the structure of both reactants, are formed. For example, it has long been known (6,7) that 1,3,4-thiadiazoles are produced from thiocarboxylic acid chlorides and diazoacetic esters or diazomethane.…”

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confidence: 99%

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

Demaree¹,

Doria²,

Muchowski³

1977

Can. J. Chem.

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The reaction of thiophosgene with α-diazocarbonyl compounds produced mixtures of 1,2,3-and 1,3,4-thiadiazoles, in which the latter predominated, irrespective of whether the bis(α-diazoacyl)mercury derivatives or the free diazo compounds were used. In contrast, ethyl chlorodithioformate gave exclusively 1,3,4-thiadiazoles with α-diazocarbonyl compounds in the presence of triethylamine and only 1,2,3-thiadiazoles when the bis(α-diazoacyl)mercury derivatives were used.

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Struktur und Reaktionen des Hydrindantins und einiger seiner Derivate

Cited by 40 publications

References 20 publications

Products of the Reactions of 2-Diazomalonate and of 2-Diazoindanedione with Germylenes and Stannylenes

Products of the Reactions of 2-Diazomalonate and of 2-Diazoindanedione with Germylenes and Stannylenes

Synthesis of Fingerprint Reagents: Aromatic Nucleophilic Substitution as a Route to 5-Substituted Ninhydrins

The reaction of certain α-diazocarbonyl compounds with thiophosgene and ethyl chlorodithioformate

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