K. Tsumori, H. Minato, Michio. Kobayashi
Nov 1, 1973
Citations
1
Influential Citations
12
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reactions of methyl-p-tolylmethoxysulfonium ion with such nucleophiles as tertiary amines, triphenylphosphine, thiophenolate anion and p-toluenesulfinate anion were investigated. The points of attack vary with nucleophile; the sulfonium ion receives nucleophilic attacks at its methoxy oxygen, methoxy carbon, sulfonium sulfur, S–CH3 hydrogen or O–CH3 hydrogen atoms. Optically active methyl-p-tolylmethoxysulfonium ion was also synthesized, and its reactions with benzylethylphenylamine, benzylmethylphenylphosphine and benzyl ethyl sulfide were studied. In the cases of the amine and the sulfide, the methylated products had optical activity. Thus, the methoxysulfonium ion can act as an optically active methylating agent.