Synthesen mit Diazomethan VII Weiteres über die Umsetzung von Aldehyden und Ketonen

Arndt, F.; Amende, J.; Ender, W.

doi:10.1007/bf01638230

Cited by 26 publications

(7 citation statements)

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“…In his second paper on this subject Heller reported obtaining a second product, possibly the isoquinoline derivative. The reaction was later studied by Arndt and coworkers (9,10). Arndt assumed that the diazomethane reacts with the /3-carbonyl group of isatin to give an addition product (I), which then rearranges to give either the ethylene oxide (II) or 2,3-dihydroxyquinoline (III or IV).…”

Section: J Reaction With Diazomethane and Hydrazoic Acidmentioning

confidence: 99%

“…The reactions of a number of substituted isatins with diazomethane have been studied by Heller (191). The reaction of 1-hydroxyisatin with diazomethane was also investigated by Arndt (9). This reaction has likewise been investigated by Ault, Hirst, and Morton Caronna (72) found that isatin and A-acetylisatin react with hydrazoic acid to give anthranilamide, while A-ethylisatin reacts similarly to give o-ethylaminobenzamide.…”

Section: J Reaction With Diazomethane and Hydrazoic Acidmentioning

confidence: 99%

See 1 more Smart Citation

The Chemistry of Isatin.

Sumpter¹

1944

Chem. Rev.

165

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Section: J Reaction With Diazomethane and Hydrazoic Acidmentioning

confidence: 99%

Section: J Reaction With Diazomethane and Hydrazoic Acidmentioning

confidence: 99%

The Chemistry of Isatin.

Sumpter¹

1944

Chem. Rev.

165

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“…C6H6COCOC6H6 + ch2n2-> ¿ 0 +n2 ch2 Anthraquinone does not react, but phenanthraquinone with diazomethane plus a trace of methanol gives the ethylene oxide (IV) (19) which, when treated with hydrochloric acid in methanol, gives the chlorohydrin, thus establishing the structure. The acetal (V) is obtained if much methanol is used.…”

Section: C6h5c=-cc6h5mentioning

confidence: 99%

“…. of p-nitrobenzaldehyde there was produced 5 g. of the ethylene oxide, 3.2 g. of p-nitroacetophenone, and traces of p-N0206 40 2000 3(19).The mechanism for these reactions suggested by Arndt (seealso 226, 227) involves a primary 1,3-addition: , possibly via cyclopropanone (217) as an intermediate, while diphenylketene reacts with diazoacetic ester as follows (346):…”

mentioning

confidence: 99%

Aliphatic Diazo Compounds, Nitrones, and Structurally Analogous Compounds. Systems Capable of Undergoing 1,3-Additions.

Smith¹

1938

Chem. Rev.

138

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“…Chloroacetone and diazomethane react to form chloroisobutylene oxide, CH2C(CH3)CH2C1 0 b.p. 124°C., and a mixture of higher oxides (10). NNHC0NHC6H4N02, prepared by mixing chloroacetone with m-nitrophenylsemicarbazide hydrochloride, forms pale yellow needles melting to a semi-solid at 223°C.…”

Section: Ch3coch2cimentioning

confidence: 99%

Lachrymators.

Jackson¹,

Jackson²

1935

Chem. Rev.

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Many chemical compounds possess more or less lachrymatory properties varying in intensity from mild irritation to severe, with a flow of tears so copious as to blind the victim temporarily. Some of these compounds, like chloropicrin, are also toxic. The lachrymatory property seems to be connected with the halogen group, and all lachrymators contain one of the halogens. In general, those compounds containing iodine have the strongest lachrymatory effect; bromine compounds are less powerful and chlorine compounds still less effective (304). The comparative rarity and expense of iodine makes the use of this element impractical. Most of the lachrymators used during the World War contained bromine and some, like bromobenzyl cyanide, were extremely effective. But bromine is quite expensive as compared with chlorine, and the development of the lachrymator chloroacetophenone, which is as effective as bromobenzyl cyanide, makes it appear probable that in the future no other lachrymatory gas will be manufactured. It is an interesting fact that even as early as 1887 Prof. Bayer, in his lectures to advanced students, included a reference to the military value of lachrymators (180). When tear gas is referred to by the general public, chloroacetophenone is usually meant.The chemical agents introduced during the World War proved very effective, as shown by the reports of the War Departments of the countries involved and the increased number of gas shells fired during the latter part of the war. Despite these facts, there is still an unholy fear of such agents on the part of the average citizen, owing to the mass of war propaganda against the use of gas and the lack of accurate information concerning same.Men fear the unknown; it is easier for them to maintain morale in the face of bullets, naked bayonets, and the sword's edge than in the presence of invisible gas; likewise a mob has less fear of the fire hose, night clubs, and bullets than of gas. There is always the uncertainty in their minds as to the effects of the gas, and more especially if there be a little smoke mixed with it, for they know not what may be behind it. The only real danger of serious injury from using non-toxic tear gas is from the possibility that members of the crowd may be trampled upon in attempts to escape. 195

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Synthesen mit Diazomethan VII Weiteres über die Umsetzung von Aldehyden und Ketonen

Cited by 26 publications

References 0 publications

The Chemistry of Isatin.

The Chemistry of Isatin.

Aliphatic Diazo Compounds, Nitrones, and Structurally Analogous Compounds. Systems Capable of Undergoing 1,3-Additions.

Lachrymators.

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