62992-33-0Relevant academic research and scientific papers
Triethylsiloxymethyl-N,N-dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O–H, S–H, P–H and Aromatic C–H Systems
Gonzalez, Paulina E.,Sharma, Hemant K.,Chakrabarty, Sanchita,Metta-Maga?a, Alejandro,Pannell, Keith H.
, p. 5610 - 5616 (2017/10/13)
Triethylsiloxymethylamine, Et3SiOCH2NMe2, readily synthesized in high yield by the hydrosilylation reaction between Et3SiH and DMF, is an excellent (N,N-dimethylamino)methyl transfer agent to a representative range of aliphatic alcohols, thiols, and Ph2PH (E–H) materials. The reactions are almost instantaneous at room temperature in inert solvents and require no activating agents to produce E–CH2NMe2 products in high yields and illustrate the title compound as an excellent addition to the family of organic reagents. For aromatic alcohols, electrophilic substitution of the aromatic ring occurs in high yield. Crystal structures of new materials such as the cholestero–CH2NMe2 derivative, 2–4-[bis(N,N-dimethylamino)methyl]-1-naphthol, and the phosphine oxide derived from Ph2PCH2NMe2 are reported.
The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles
Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
, p. 2941 - 2958 (2007/10/03)
Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.
A New Convenient Synthesis of Dialkyl(methylene)ammonium Chloride
Rochin, C.,Babot, O.,Dunogues, J.,Duboudin, F.
, p. 228 - 229 (2007/10/02)
A new, convenient synthesis of dialkyl(methylene)ammonium chloride is proposed from gem-aminoethers and methyltrichlorosilane, a by-product of the industrial methylchlorosilane synthesis.
CIDNP STUDY OF THE PHOTOCLEAVAGE OF BENZYL DERIVATIVES
Gardini, G. P.,Charlton, J. L.,Bargon, J.
, p. 987 - 990 (2007/10/02)
Evidence of the mechanistic pathways involved in the acetone sensitized homolytic photocleavage of benzyltrialkylammonium salts and other benzyl derivatives is obtained by CIDNP.
