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

Kiyomi Kakiuchi*, Bunji Yamaguchi, Tobe Yoshito

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Irradiation of 1-naphthol (la) 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 41–72% yields. Irradiation of la with AlBr3 in CH2Br2 afforded (bromomethyl)indanone 5a in 54%. 3-Methyl derivative le was unreactive and 4-methyl derivative lf underwent isomerization to 1e.

Original languageEnglish
Pages (from-to)5745-5747
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number20
DOIs
StatePublished - 1 Sep 1991

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