Regioselective Alkylation of Anthrahydroquinone and Anthrone in Water with Quinonemethides and Other Alkylating Agents

DOI: 10.1021/jo00340a006

Source and publish data:

Journal of Organic Chemistry p. 22 - 29 (1982)

Update date:2022-07-31

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Authors:

Dimmel, Donald R.

Shepard, Donaline

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Article abstract of DOI:10.1021/jo00340a006

Antrahydroquinone (AHQ) and anthrone are alkylated in the C10 position by quinonemethides, generated in situ from p-acetoxybenzyl chlorides, to give adducts 13-15, 24, 25, 28, 29, and 32.Aqueous alkylations of AHQ with methyl vinyl ketone, cinnamaldehyde, and benzyl chloride also produces C10-substituted 10-hydroxyanthrones.Simple ketones and aldehydes do not, however, alkylate AHQ in aqueous alkali.

Full text of DOI:10.1021/jo00340a006

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