Category: 29809-13-0

A new method for the preparation of cyclic nitriles by catalytic degradation. I was written by Houben, J.;Fischer, Walter. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1930.Computed Properties of C11H11N This article mentions the following:

The trichloromethyl ketimides of the type described in the preceding abstract are smoothly converted not only by alc. and aqueous alkali but also catalytically in Et₂O by small amounts of powd. KOH into cyclic nitriles and CHCl₃ without the alkali being in any way attacked. With the ketimides of the free phenols, where the HO group must be saturated with alkali before cleavage can take place, it is difficult to determine the amount of alkali required for the cleavage, but it is believed that here, too, the process is catalytic. A procedure has been developed which permits of converting the ketimide directly, without purification, into the nitrile and also of separating the ketimide from the accompanying ketone. The method almost always gives good yields and has thus far failed in no case. Thus, from p-MeC₆H₄C(:NH)CCl₃ (85% pure), allowed to stand 2-4 hrs. under petroleum ether with powd. CaO and KOH (powd. under petroleum ether and dried over P₂O₅ at 100鎺?, was obtained 75% p-MeC₆H₄CN which, while it did not solidify until cooled to 0鎺? yielded only p-MeC₆H₄CO₂H with acids and then alkali, and p-MeC₆H₄CONH₂ with MeOH-HCl. It is not clear what caused the depression of the m. p. of the MeC₆H₄CN. The crude mixture of 2,4-Me₂C₆H₃C(:NH)CCl₃ (91%) and ketone obtained from m-xylene and CCl₃CN gives with powd. KOH-CaO 82% 2,4-Me₂C₆H₃CN, m. 24-5鎺? From 2,5-Me₂C₆H₃C(:NH) CCl₃ (85%) was obtained 98% 2,5-Me₂C₆H₃CN, begins to m. -3鎺? m. completely 6鎺? 2,4,6-Me₃C₆H₂CN, b. 225-30鎺? was obtained in 62% yield, based on the C₆H₃Me₃ used, without isolating the ketimide. The mixture of little 浼? with much 灏? tetralyl CCl₃ ketimide HCl salts (see preceding abstract) yields 14% 浼?cyanotetralin, m. 48-50鎺?the H₂O set free from the salts by the KOH converting the 灏?ketimide almost completely into the ketone and NH₈, which is recovered in about 68% yield as C₁₀H₁₁CO₂K. p-HOC₆H₄C(:NH.HCl)Me, allowed to stand 2 min. in 10% NaOH at 50鎺? gave p-HOC₆H₄CO₂H and 25% p-HOC₆H₄CN. 2,5,4-Me₂(HO)C₆H₂C(:NH)CCl₃ was quant. converted in the same way into Me₂(HO)C₆H₂CN, m. 163-5鎺? 2,6,Dimethyl-4-methoxy- benzonitrile, m. 85-7鎺? was obtained in 52% yield, together with a substance, m. 49-55鎺? of the same N content, directly from 3,5-Me₂C₆H₃OMe without isolating the ketimide. p-Thymotinic nitrile, m. 115-6鎺? was obtained in 81% yield from the ketimide-HCl, and in 61% yield directly from thymol. p-Carvacrotinic nitrile, m. 75-7鎺? was likewise obtained in 62% yield from the ketimide-HCl. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0Computed Properties of C11H11N).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C閳ユ弲 bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Computed Properties of C11H11N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Charge localization in the retro-Diels-Alder fragmentation of tetralins was written by Lightner, David A.;Steinberg, Frank S.. And the article was included in Organic Mass Spectrometry in 1970.SDS of cas: 29809-13-0 This article mentions the following:

The electron-impact induced retro-Diels-Alder reaction of 5- and 6-substituted tetralins has been examined Most electron-donating groups at C-5 retard the fragmentation relative to tetralin; whereas, electron-withdrawing groups slightly increase the fragmentation. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0SDS of cas: 29809-13-0).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.SDS of cas: 29809-13-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts