6926-42-7Relevant academic research and scientific papers
Orthoamides and iminium salts LXXIV [1]. Reactions of N,N,N',N'- Tetramethyl-chloroformamidiniumChloride with metals
Kantlehner, Willi,Aichholz, Reiner,Karl, Martin
, p. 305 - 319 (2012/07/13)
N,N,N',N'-Tetramethyl-formamidinium chloride (2a) reacts with elemental sodium in various solvents to give N,N,N',N',N'',N''-hexamethyl-guanidinium chloride (4a). The reaction of 2a with potassium affords N,N,N',N',N'',N'',N''', N'''-octamethyl-oxamidinium dichloride (3a). From the reaction of 2a with magnesium in different solvents in general result mixtures of the salts 4a, 3a and N,N,N',N'-tetramethyl-formamidinium chloride (10a). The composition of these mixtures depends on the solvent and the reaction temperature. Similar results are obtained, when a zinc'copper couple is used instead of magnesium. Very likely from 2a and magnesium or zinc, respectively, organometallic intermediates 11, 12 are formed which could be trapped by aromatic aldehydes and phenylisocyanate. The salt 2a can be reductively coupled by a low-valent titanium reagent to give the oxamidinium salt 3a.
Orthoamides, XL. - Preparation of 1,1,2,3,3-Pentasubstituted and 1,1,2,2,3,3-Hexasubstituted Guanidinium Salts and 1,1,2,3,3-Pentaalkylguanidines
Kantlehner, Willi,Haug, Erwin,Mergen, Walter W.,Speh, Peter,Maier, Thomas,et al.
, p. 108 - 126 (2007/10/02)
N,N,N',N'-(Tetramethyl)thiourea (1) reacts with N,N-dimethylcarbamoyl chloride (2) to give the guanidinium salt 3a.The carbenium salt 4, obtained from 1 and dimethyl sulfate, affords on treatment with dimethylamine the guanidinium salt 3b.Reaction of phosgene with N,N,N',N'-tetraalkylureas yields the chloroformamidinium chlorides 5 which are transformed by mixtures of primary or secondary amines and tertiary amines into mixtures of guanidinium salts and ammonium salts.From these mixtures, by means of sodium hydroxide, have been isolated the guanidinium salts 3a, 6, and 11, respectively.Some of the salts 3a and 6 are converted into the corresponding tetraphenylborates 7.The fluoroborates 8a and 8b are obtained from guanidinium chlorides 3a and 6h, respectively.By anion exchange in 8a, b the salts 9, 10 have been prepared.Alkylation of the guanidines 12 affords the guanidinium salts 13.
Orthoamides, XXXIX. - Preparation of Ketene Aminals from CH-acidic Compounds and Ethoxy-N,N,N',N',N'',N''-hexamethylmethanetriamine
Kantlehner, Willi,Mergen, Walter W.,Haug, Erwin
, p. 290 - 298 (2007/10/02)
The orthocarbonic acid derivative 5 reacts with the weakly CH-acidic compounds 4a-h to give the ketene aminals 6a-h.The compound 6i has been obtained from 4i and N,N,N',N',N'',N''-hexamethylguanidinium chloride in the presence of sodium hydride.Acetone re
