Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

Yasuhiro Maeda, Naohiro Shirai, Yoshiro Sato, Hiroshi Tatewaki

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


Reaction of N,N-dimethyl-N-[(trimethylsilyl)methyl](polymethoxy-substituted benzyl)ammonium iodides 1a-e with cesium fluoride gave polymethoxy-substituted 5-[(dimethylamino)methyl]-6-methylene-1,3-cyclohexadienes 3 and 5 ([2,3] sigmatropic rearrangement products). However, these were quickly hydrolyzed to polymethoxytoluenes 8 during the aqueous workup. The pathway of the hydrolysis of 3 and 5 is discussed.

Original languageEnglish
Pages (from-to)7897-7901
Number of pages5
JournalJournal of Organic Chemistry
Issue number25
Publication statusPublished - 01-12-1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


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