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

DOI: 10.1021/jo00296a039

Source and publish data:

Journal of Organic Chemistry p. 2767 - 2770 (1990)

Update date:2022-09-26

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Authors:

Shirai, Naohiro

Watanabe, Yoko

Sato, Yoshiro

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Article abstract of DOI:10.1021/jo00296a039

Formation of benzylammonium N-methylides by fluoride anion induced desilylation of dimethyl(4-substituted benzyl)<(trimethylsilyl)methyl>ammonium halides (1) and 3-substituted benzyl analogues (6) was examined to isolate 5-<(dimethylamino)methyl>-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.

Full text of DOI:10.1021/jo00296a039

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