Issue 0, 1974

Photochemistry of 2-(cycloalk-1-enyl)cycloalkanones. A new photochemical reaction of βγ-unsaturated ketones

Abstract

On u.v. irradiation 2-(cyclohex-1-enyl)cyclohexanone (2) reacts by γ-hydrogen abstraction by the carbonyl oxygen atom and cyclobutane formation to form tricyclo[6.4.0.02,7]dodec-6-en-1-ol (4). In contrast, 2-(cyclohept-1-enyl)cycloheptanone (11) or 2-(cyclo-oct-1-enyl)cyclo-octanone (13) undergoes oxetan formation between the two double bonds giving 2-oxatetracyclo[8.5.0.01,9.03,9]pentadecane (12) or 2-oxatetracyclo[9.6.0.01,10.03,10]-heptadecane (14), respectively.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1974, 1037-1043

Photochemistry of 2-(cycloalk-1-enyl)cycloalkanones. A new photochemical reaction of βγ-unsaturated ketones

R. C. Cookson and N. R. Rogers, J. Chem. Soc., Perkin Trans. 1, 1974, 1037 DOI: 10.1039/P19740001037

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