ChemInform Abstract: THE CHEMISTRY OF CYCLOHEPTADIENONES, PART VIII. THE FORMATION OF CYCLOHEPTENONE AND CYCLOHEPTADIENONES FROM BICYCLO(3.2.0)HEPTANONE DERIVATIVES. AN ACID-CATALYZED, TWO CARBON RING EXPANSION REACTION

1976 ◽  
Vol 7 (22) ◽  
pp. no-no
Author(s):  
KENNETH E. HINE ◽  
RONALD F. CHILDS
Keyword(s):  
Ring Expansion ◽  
Carbon Ring ◽  
Acid Catalyzed ◽  
Ring Expansion Reaction

The formation of cycloheptenone and cycloheptadienones from bicyclo[3.2.0]heptanone derivatives. An acid-catalyzed, two carbon ring expansion reaction

1976 ◽  
Vol 54 (1) ◽  
pp. 12-18 ◽  
Author(s):  
Kenneth E. Hine ◽  
Ronald F. Childs
Keyword(s):  
Ring Expansion ◽  
Membered Ring ◽  
Acid Solutions ◽  
Ring Expansions ◽  
Carbon Ring ◽  
Ether Mixture ◽  
Synthetic Utility ◽  
Acid Catalyzed ◽  
Ring Expansion Reaction ◽  
Strong Acids

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.

Synthesis of cyclodec-3-en-1-ols by acid-catalyzed two-carbon ring expansion

1973 ◽  
Vol 38 (9) ◽  
pp. 1758-1759 ◽  
Author(s):  
Richard W. Thies ◽  
James E. Billigmeier
Keyword(s):  
Ring Expansion ◽  
Carbon Ring ◽  
Acid Catalyzed
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