The formation of cycloheptenone and cycloheptadienones from bicyclo[3.2.0]heptanone derivatives. An acid-catalyzed, two carbon ring expansion reaction
作者:
Kenneth E. Hine,
Ronald F. Childs,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1976)
卷期:
Volume 54,
issue 1
页码: 12-18
ISSN:0008-4042
年代: 1976
DOI:10.1139/v76-004
出版商: NRC Research Press
数据来源: NRC
摘要:
In strong acids, such as FSO3H and 96% H2SO4, bicyclo[3.2.0]heptan-6-one and bicyclo[3.2.0]hept-2-en-7-one undergo a clean isomerization to form protonated cyclohept-2-enone and cyclohepta-2,4-dienone, respectively. Substituted derivatives undergo comparable ring expansions when dissolved in these strong acids. The seven-membered ring ketones can be recovered on quenching the acid solutions with a NaHCO3–ether mixture. In contrast, bicyclo[3.2.0]hept-2-en-6-one when dissolved in FSO3H rearranged to give protonated 1-acetylcyclopentadiene. The mechanism and synthetic utility of these reactions is discussed.
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