Comparison of the reaction of benzylammonium N-methylides with that of benzylsulfonium S-methylides

Tomofumi Nishimura, Chen Zhang, Yasuhiro Maeda, Naohiro Shirai, Shin ichi Ikeda, Yoshiro Sato

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Allylbenzylsulfonium S-methylides 8S and dibenzylsulfonium S-methylides 18S have been generated by the fluoride ion-induced desilylation of S- benzyl-S-[(trimethylsilyl)methyl](alk-2-enyl)sulfonium salts 4S and S- benzyl-S-[(trimethylsilyl)methyl](4-substituted benzyl)sulfonium salts 7S, and the isomerized products are compared with those of the corresponding N- methylides. S-Methylides 8S selectively rearrange toward the allyl groups (path a in Chart 2), whereas rearrangement to the benzyl groups (path b) competitively occurs in N-methylides 8N. Isomerization of S-methylides 18S to S-benzylides 19S and 20S competes with sigmatropic rearrangement to the benzyl groups (paths a and b in Chart 3), whereas the isomerization of N- methylides 18N is not observed.

Original languageEnglish
Pages (from-to)267-272
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number2
DOIs
Publication statusPublished - 02-1999

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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