An Unusual γ-Silyl Effect in TiCl4-Catalyzed Arylation of 1,4-Benzoquinones

DOI: 10.1021/jo00023a005

Source and publish data:

Journal of Organic Chemistry p. 6491 - 6494 (1991)

Update date:2022-08-03

Topics:

Authors:

Engler, Thomas A.

Reddy, Jayachandra P.

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Article abstract of DOI:10.1021/jo00023a005

Cyclopropylbenzene (1c) reacts with 2-methoxy-1,4-benzoquinone in the presence of TiCl4 to give 2-(4'-cyclopropylphenyl)-5-methoxy-1,4-benzoquinone in moderate yield (46percent).Considerable improvement in yield (69percent) is observed in reactions of trans-2-phenyl-1-(trimethylsilyl)cyclopropane (1a) with the TiCl4-quinone complex.

Full text of DOI:10.1021/jo00023a005

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Product name:2-[4-((1S,2R)-2-Trimethylsilanyl-cyclopropyl)-phenyl]-[1,4]benzoquinone

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