Rearrangement of (Polymethoxybenzyl)ammonium N-Methylides

DOI: 10.1021/jo00104a055

Source and publish data:

Journal of Organic Chemistry p. 7897 - 7901 (1994)

Update date:2022-08-04

Topics:

Authors:

Maeda, Yasuhiro

Shirai, Naohiro

Sato, Yoshiro

Tatewaki, Hiroshi

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Article abstract of DOI:10.1021/jo00104a055

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.

Full text of DOI:10.1021/jo00104a055

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