72443-52-8Relevant academic research and scientific papers
A Convenient Synthesis of o-Methylbenzylamine Derivatives from Benzyl Halides: The Improved Sommelet-Hauser Rearrangement
Nakano, Mitsuji,Sato, Yoshiro
, p. 1684 - 1685 (2007/10/02)
Desilylation by fluoride anion of benzyldimethyl(trimethylsislylmethyl)ammonium halides having a Cl(1-), CN(1-), or AcO(1-) substituent on the benzene ring gave high yields of the Sommelet-Hauser rearrangement products at room temperature.
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.
