15848-75-6

Upstream product

• 100-97-0 hexamethylenetetramine 
• 13651-55-3 2,3-dimethylbenzyl chloride 
• 117867-97-7 N,N,N-trimethyl-1-(o-tolyl)methanaminium iodide 
• 51180-51-9 But-2-ynyl-dimethyl-((E)-penta-2,4-dienyl)-ammonium; bromide 
• 102101-47-3 Dimethyl-(2-methyl-benzyl)-trimethylsilanylmethyl-ammonium; bromide 
• 4525-48-8 N,N-dimethyl(2-methylbenzyl)amine 

Downstream Products

• 7509-54-8 <2,3-Dimethyl-benzyl>-<2-hydroxy-aethyl>-dimethyl-ammoniumbromid 
• 7596-03-4 <2,3-Dimethyl-benzyl>-<2-hydroxy-propyl>-dimethyl-ammoniumbromid 

Relevant academic research and scientific papers

Rearrangement of (Substituted benzyl)trimethylammonium Ylides in a Nonbasic Medium: The Improved Sommelet-Hauser Rearrangement

Benzyl quaternary ammonium ylide formation in a nonbasic medium was accomplished by fluoride anion induced desilylation of benzyldimethylammonium bromide (3a) and ortho- or para-substituted benzyl analogues 3b-k.Treatment of 3 with CsF in HMPA at room temperature gives high yields of the Sommelet-Hauser rearrangement products 7 from 3a and methyl-, acetoxy-, and chloro-substituted analogues 3b-f.However, formation of the Stevens rearrangement products 8 is competitive for the reaction of compounds 3g-k having strong electron-withdrawing substituents such as acetyl, cyano, and nitrogen groups.From the o-cyano-substituted analogue 3h, a considerable amount of para Sommelet-Hauser rearrangement product is isolated.

A Convenient Synthesis of o-Methylbenzylamine Derivatives from Benzyl Halides: The Improved Sommelet-Hauser Rearrangement

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.