Trimethylamine formate

Trimethylammonium formate (Trimethylamine formate) [1, 1231], Supplier Eastman. 

Interconversion of the four tautomeric azepines. either by [1,5]-H sigmatropic shifts, or under base catalysis, is common and almost always results in the formation of a 3//-azepine. For example, 1 //-azepine (1) in the presence of trimethylamine isomerizes rapidly to the 3H-tautomer 2 accompanied by formation of some polymer.9... 

Hippe H, D Caspari, K Fiebig, G Gottschalk (1979) Utilization of trimethylamine and other N-methyl compounds for growth and methane formation by Methanosarcina barkeri. Proc Natl Acad Sci USA 76 494-498. 

A mixture containing 15.7% of sodium borohydride in DMF decomposed when it was heated by forming trimethylamine. The temperature of the solid residue formed rose to 310°C. This interaction occurs after a period of induction, which depends on temperature (45 hours at 62°C 45 minutes at 90°C). This period is reduced, if formic acid is present because of the formation of the F320 salt (according to the authors). 

The Mulliken theory of overlap and orientation principle (cf. Chap. 2) predicts that stabilization in the molecular complex formation should essentially be determined by the overlap of the donor HO and the acceptor LU. The iodine complex of trimethylamine will take the form... 

Reaction of [Pt3(/u-S02)3 P(Cy)3 3] with 2,6-xylyl isocyanide results in displacement of one or at most two of the S02 ligands by the isocyanide.21 Similarly, carbon monoxide usually only partially displaces the S02, but the addition of trimethylamine /V-oxide (Me3NO) facilitates the substitution leading to formation of [PtsQx-COjsfPlCyjs js].22 Me3NO also facilitates substitution of one S02 ligand by halides and azide.2... 

Group contribution method of Andersen, Beyer, and Watson [51,52] In this method, a given compound is constructed from abase group (methane, cyclopentane, benzene, naphthalene, methylamine, dimethylamine, trimethylamine, or formamide) with known enthalpies of formation, which is then modified by appropriate substitutions to yield the desired molecule. 

Irradiation of 8 with trimethylamine 11 yields the regiospecific adducts 13, 17 and 2027. The reaction of 8 with triethylamine 10 in either hexane or acetonitrile solution (>290 nm) results in the formation of a single adduct 14 (24% yield) accompanied by comparable amounts of 17 (15%) and also 20 (78%)28 (equation 3). Regiospecific addition of triethylamine to a-methylstyrene 9 is also observed to give 15 (32%), 18 (11%) and 21 (8%)26 (equation 3). 

Other bases found to react with 1,1,1-trinitroethane via formation of 1,1-dinitroethene include trimethylamine, guanidine and diethylmalonate anion (152), the latter forming (153) in 36 % yield. Shechter and Zeldin found no correlation as to why some bases react with 1,1,1-trinitroethane so differently to others but noted that simple alkoxides, aliphatic amines, guanidine, cyanide and malonate anions reacted via the 1,1-dinitroethene pathway. 

Trimethylamine replaces PH3 quantitatively in BH3 PH3 to give BH3 N(CH3)3. Liquid or gaseous ammonia also replaces phosphine in the compound BH3 PH3 to the extent of 52-58% or up to 75%, respectively. The hydrogen atoms bonded to boron are partially, or completely, replaced by chlorine on treatment with hydrogen chloride, depending on the reaction conditions. The first stage of the reaction with hydrogen chloride is the formation of the colourless, viscous liquid BHjCl PH3 (see below). 

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