Issue 17, 1996

Photoisomerization of 5,5-dimethyl-3-(3,3-dimethylbut-1-nyl)-2-(pent-4-enyl)-cyclohex-2-enone to tert-butyl-(4,4-dimethyl-2-oxotricyclo[7.3.0.01,6] dodec-6-en-7-yl)carbene

Abstract

On irradiation (λ > 340 nm) cyclohexenone 1 is converted to a mixture of diastereoisomeric 4,4-dimethyl-7-(2,2-dimethylcyclopropyl)tricyclo[7.3.0.0 1,6]dodec-6-en-2-ones 2 via the title Carbene 4, which can also be efficiently trapped both by methanol or by oxygen to afford methyl ethers 5a and 5b or the pivaloyl derivative 6, respectively.

Article information

Article type
Paper

Chem. Commun., 1996, 2065-2065

Photoisomerization of 5,5-dimethyl-3-(3,3-dimethylbut-1-nyl)-2-(pent-4-enyl)-cyclohex-2-enone to tert-butyl-(4,4-dimethyl-2-oxotricyclo[7.3.0.01,6] dodec-6-en-7-yl)carbene

B. Kisilowski, W. C. Agosta and P. Margaretha, Chem. Commun., 1996, 2065 DOI: 10.1039/CC9960002065

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