Novel Photochemical Ring Contraction of 1-Naphthols Promoted by Aluminum Halides

DOI: 10.1021/jo00020a005

Source and publish data:

Journal of Organic Chemistry p. 5745 - 5747 (1991)

Update date:2022-07-29

Topics:

Authors:

Kakiuchi, Kiyomi

Yamaguchi, Bunji

Tobe, Yoshito

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Article abstract of DOI:10.1021/jo00020a005

Irradiation of 1-naphthol (1a) and its 2-alkyl and 6-methoxy derivatives 1b-d with 5 equiv of AlCl3 or AlBr3 in CH2Cl2 gave (chloromethyl)indanones 4a-d in 41-72percent yields.Irradiation of 1a with AlBr3 in CH2Br2 afforded (bromomethyl)indanone 5a in 54percent. 3-Methylderivative 1e was unreactive and 4-methyl derivative 1f underwent isomerization to 1e.

Full text of DOI:10.1021/jo00020a005

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