Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process.
We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90064-1569, USA. jung@chem.ucla.edu
Yoo
Dongwon
D
D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000475:Alkenes; D003517:Cyclopentanes; C013905:cyclopentenone