72443-57-3Relevant academic research and scientific papers
Aminosilylation of aldehydes mediated by lithium perchlorate: Novel method for synthesis of α-silylamines
Naimi-Jamal, Reza,Mojtahedi, Mohammad M.,Ipaktschi, Junes,Saldi, Mohammad R.
, p. 3709 - 3711 (2007/10/03)
α-Silylated N,N-dialkylamines 7a-k were easily synthesized in good to excellent yields from aldehydes 1, (trimethylsilyl)dialkylamines 2, and phenyldimethylsilyllithium 4, diphenylmethylsilyllithium 5, or triphenylsilyllithium 6, in concentrated ethereal
Application of 13C NMR Spectroscopy and 13C-Labeled Benzylammonium Salts to the Study of Rearrangements of Ammonium Benzylides
Zdrojewski, Tadeusz,Jończyk, Andrzej
, p. 452 - 457 (2007/10/03)
Ylides generated from N-(cyanomethyl)-N,N-dimethyl-N-[α-(trimethylsilyl)benzyl]ammonium chloride (4) and fluoride anion afford the products of [1,2] shift 11 and [2,3] shift 13. Formation of product 13 shows that, in the presence of water from TBAF, rearrangements and [1,3]H shift in ylide intermediates become competitive processes. The reaction of N-benzyl-N,N-dimethyl-N-[α-(trimethylsilyl)benzyl]ammonium bromide (5) and 13C labeled (at the benzyl carbon) salt 5* gave a mixture of 10, 14, and 15 as products of [1,4], [1,2], and [2,3] rearrangement, respectively. 13C NMR spectra of products derived from salt 5* exclude [1,3]H shift in ylide 9a+-. Rearrangement of ylides generated from N-benzyl-N,N-dimethyl-N-[(dimethylphenylsilyl)methyl]ammonium bromide (6*) (enriched in 13C at benzyl carbon) and n-BuLi reveals that N,N-dimethyl-2-[(dimeth-ylphenylsilyl)methyl]benzylamine (20*) is not formed by a [1,4] shift but instead, via a [2,3] shift in silylmethylide followed by subsequent [1,4]Si and [1,2]H shift, as previously suggested in the literature. This mechanism is unique to some silyl-substituted ylides.
Ylide Reactions of Benzyldimethylammonium Halides
Sato, Yoshiro,Yagi, Yoko,Koto, Masami
, p. 613 - 617 (2007/10/02)
Deprotonation of benzyldimethylammonium halides (10) with sodium amide or n-butyllithium afforded silylated ylide intermediates 11, which were rearranged into N,N-dimethyl-2-benzylamines (13) accompanied by the formation of Sommelet-Hauser and Stevens rearrangement products (12 and 22).The ylide formation by the cleavage of carbon-silicon bonds also is discussed in the reaction of 10 with sodium amide and lithium aluminum hydride.
