Synthesis of Tricyclo [6.2.1.0<sup>1,5</sup>]undecadiones <i>via</i> Intramolecular Photoaddition of 5-(1-Cyclopentenylmethyl)-3-alkoxy-2-cyclopentenones

Von Oppolzer, Wolfgang; Burford, Sidney C.

doi:10.1002/hlca.19800630406

Scientific article

English

Synthesis of Tricyclo [6.2.1.0^1,5]undecadiones via Intramolecular Photoaddition of 5-(1-Cyclopentenylmethyl)-3-alkoxy-2-cyclopentenones

ContributorsVon Oppolzer, Wolfgang; Burford, Sidney C.

Published inHelvetica chimica acta, vol. 63, no. 4, p. 788-792

Publication date1980-06-06

Abstract

Irradiation of the dienone methyl ether 3a furnished the unstable regioisomeric photoadducts 4a and 5a which on Lewis acid-catalyzed fragmentation afforded the tricyclic diketones 6,7 and 8. The same mixture was obtained from the isobutyl ether 3b (Scheme 2).

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, BURFORD, Sidney C. Synthesis of Tricyclo [6.2.1.0^1,5]undecadiones via Intramolecular Photoaddition of 5-(1-Cyclopentenylmethyl)-3-alkoxy-2-cyclopentenones. In: Helvetica chimica acta, 1980, vol. 63, n° 4, p. 788–792. doi: 10.1002/hlca.19800630406

Article (Published version)

Identifiers

PID : unige:169440
DOI : 10.1002/hlca.19800630406

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19800630406

Journal ISSN0018-019X

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Synthesis of Tricyclo [6.2.1.01,5]undecadiones via Intramolecular Photoaddition of 5-(1-Cyclopentenylmethyl)-3-alkoxy-2-cyclopentenones

Irradiation of the dienone methyl ether 3a furnished the unstable regioisomeric photoadducts 4a and 5a which on Lewis acid-catalyzed fragmentation afforded the tricyclic diketones 6,7 and 8. The same mixture was obtained from the isobutyl ether 3b (Scheme 2).

Technical informations

Synthesis of Tricyclo [6.2.1.0^1,5]undecadiones via Intramolecular Photoaddition of 5-(1-Cyclopentenylmethyl)-3-alkoxy-2-cyclopentenones