Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 8, Pages 4379-4385Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00432
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Funding
- NSF [CHE-1265843]
- Wayne State University
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1265843] Funding Source: National Science Foundation
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Two CuCN-mediated rearrangement reactions of allenylcyclopropanols to cyclopentenones have been achieved by means of Et2Zn/CuCN center dot 2LiCl or CuCN center dot 2LiCl to afford 5-alkyl or 4-alkyl cydopentenone regioisomers: the former conditions afford 5-alkyl substituted cyclopentenones via beta-carbon elimination, whereas the latter result in the 4-alkyl substituted regioisomers with concomitant oxidation at the gamma-position, via a free radical mechanism.
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