1963
DOI: 10.1002/anie.196301441
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(Halogenomethyl)pyridines and (Halogenomethyl)quinolines

Abstract: The nonspecific acid hydrolysis of proteins in aqueous solution becomes a subtratespecific reaction within layer silicates that are capable of swelling. The specificity depends, on the one hand, on the number and distribution of the negative charges in the silicate sheet, and, on the other, on the number and distribution of the c-amino-and guanido groups in the protein. Plausible menon as well [a]. Investigations with these enzyme models are, however, made difficult by the fact that they are only slightly stab… Show more

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Cited by 24 publications
(5 citation statements)
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“…Our initial research was directed toward chloride 4 , which would be a precursor to the alkylating agent, iodide 8 . There are a variety of potential short routes to α-chloropicolines from picolines; however, the majority of these feature N -oxides as prominent intermediates and were unlikely to form efficiently from electron-deficient rings such as 3 . Most of the remaining one-step procedures require chlorine gas, presenting operational hazards in our scale-up facilities that we decided to forego.…”
mentioning
confidence: 99%
“…Our initial research was directed toward chloride 4 , which would be a precursor to the alkylating agent, iodide 8 . There are a variety of potential short routes to α-chloropicolines from picolines; however, the majority of these feature N -oxides as prominent intermediates and were unlikely to form efficiently from electron-deficient rings such as 3 . Most of the remaining one-step procedures require chlorine gas, presenting operational hazards in our scale-up facilities that we decided to forego.…”
mentioning
confidence: 99%
“…The retail price of technically available BT (e.g., Marlotherm LH as a registered trademark of Sasol Germany GmbH) is US $7–8 per kilogram. We are now pursuing a cheaper synthesis protocol at a scale of several tons based on the direct chlorination of 2‐methylpyridine …”
Section: Figurementioning
confidence: 99%
“…Ther etail price of technically availableB T( e.g., Marlotherm LH as ar egistered trademarko fS asol Germany GmbH)i sU S$7-8 per kilogram.W ea re now pursuing ac heaper synthesis protocol at as cale of several tons based on the direct chlorination of 2-methylpyridine. [8] The molecular weights of the as-prepared MBP and its perhydro product, 2-[(n-methylcyclohexyl)methyl]piperidine isomers (H 12 -MBP),w ere measured by high-resolutionm ass spectrometry to be 183.1124 (calcd for C 13 H 13 N: 183.1126) and 195.2064( calcd for C 13 H 25 N: 195.2065), respectively ( Figure S2). This represents at heoretical H 2 storagec apacityo f6 .15 wt %, similar to the pairs toluene/methylcyclohexane (6.12 wt %) and BT/H 12 -BT (6.22 wt %).…”
mentioning
confidence: 99%
“…[20] However, phosphinylation of C sp3 in hetarylalkyl halides was not described in these works, obviously due to numerous side processes (easy hydrolysis, oxidation, intermolecular self-alkylation of the starting reagents, halogenophilic reactions S N 2Hal, S RN 1, etc.). [21] There are only sporadic reports in literature on phosphinylation of hetarylmethyl halides, which occurs in the presence of such hydrolytically unstable and flammable reagents as LDA, [22] BuLi, [22b] NaH, [22a,23] LiHMDS (Scheme 1), and requires especially dry conditions and specific equipment (Schlenk glassware).…”
Section: Introductionmentioning
confidence: 99%