First example of an enone-alkene [2+2+2] photocycloaddition: 1,3-photocycloaddition of tetramethylethylene across 2,7-cyclooctadienone

Authors
Matlin, AR Lin, SC Patel, HR Chai, MH
Citation
Ar. Matlin et al., First example of an enone-alkene [2+2+2] photocycloaddition: 1,3-photocycloaddition of tetramethylethylene across 2,7-cyclooctadienone, ORG LETT, 1(2), 1999, pp. 303-305
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
2
Year of publication
1999
Pages
303 - 305
Database
ISI
SICI code
1523-7060(19990729)1:2<303:FEOAE[>2.0.ZU;2-I
Abstract
[GRAPHICS] Irradiation of cyclooctadienone (1) in the presence of tetramethylethylene (TME) produces 9,10,10-tetramethyl-11 oxatricyclo[6.3.0.0(1,7)]undec-2- ene (7) in 33% yield, This reaction is the first example of a 1,3-cycloadditio n of an alkene across an enone system. This novel cycloaddition suggests th at there is substantial interaction between the carbonyl carbon and the bet a-enone carbon in the triplet excited state of 1.