30489-76-0

Upstream product

• 30481-23-3 allyl-(3-chloro-hexa-2,4-dienyl)-dimethyl-ammonium; bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 620-13-3 1-bromomethyl-3-methyl-benzene 
• 611-01-8 2,4-dimethyl-benzoic acid 
• 126062-60-0 Dimethyl-(3-methyl-benzyl)-trimethylsilanylmethyl-ammonium; bromide 
• 16308-92-2 2,4-dimethylbenzyl alcohol 
• 124-40-3 dimethyl amine 

Relevant academic research and scientific papers

Intermediate in Sommelet-Hauser Rearrangement of N,N-Dimethylbenzylammonium N-Methylides

Formation of benzylammonium N-methylides by fluoride anion induced desilylation of dimethyl(4-substituted benzyl)ammonium halides (1) and 3-substituted benzyl analogues (6) was examined to isolate 5--6-methylene-1,3-cyclohexadienes (isotoluene intermediates, 3,8,10) in the Sommelet-Hauser rearrangement.Some isotoluenes were isolated and their structures were confirmed by 1H NMR analysis.The stability of the isotoluenes was dependent on the electron-donating effects of the substituents on the conjugated bonds, and 3-methoxy-substituted isotoluene 3a was the most stable compound studied.

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.