Scientific article

The reaction of singlet oxygen with adamantylideneadamantane mediated by rose bengal

Published inHelvetica chimica acta, vol. 73, no. 6, p. 1653-1658
Publication date1990

The photo-oxygenation of adamantylideneadamantane (1) on siliceous supports using admixed granules of ion-exchange resin fixed to methylene blue (MB) and rose bengal (RB) gave exclusively the corresponding dioxetane derivative 2 for the former sensitizer, while the latter gave 2 and traces of the epoxide 3. RB and the charge-transfer complex produced from N-ethylcarbazole and 2,4,5,6-tetranitrofluoren-9-one both reacted with chemically generated singlet oxygen to give superoxide radical anion. Trapping of the latter with 5,5-dimethyl-1-pyrroline 1-oxide gave an adduct exhibiting a characteristic ESR spectrum. The treatment of 1 in MeOH with 30% aqueous H2O2 for 22 h at 60° gave 3 in 100% yield. Repetition of this experiment in the presence of 2,6-di(tert-butyl)-p-cresol caused no significant change. These results indicate that singlet oxygen reacts with 1, in the presence of RB, by two different processes. The first leads to dioxetane formation. The second process involves conversion of singlet oxygen by RB to superoxide radical anion which subsequently gives H2O2 so producing epoxide 3 from 1.

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Citation (ISO format)
JEFFORD, Charles et al. The reaction of singlet oxygen with adamantylideneadamantane mediated by rose bengal. In: Helvetica chimica acta, 1990, vol. 73, n° 6, p. 1653–1658. doi: 10.1002/hlca.19900730610
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Article (Published version)
ISSN of the journal0018-019X

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