scholarly journals Sequential cycloaddition and ring expansion reaction of arynes and methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered ring via sulfonium ylides

RSC Advances ◽  
2019 ◽  
Vol 9 (67) ◽  
pp. 39119-39123 ◽  
Author(s):  
Peng Xiao ◽  
Shikuan Su ◽  
Wei Wang ◽  
Weiguo Cao ◽  
Jie Chen ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Membered Ring ◽  
Efficient Construction ◽  
Ring Expansion Reaction ◽  
Sulfonium Ylides ◽  
Reaction Profile

Efficient construction of benzo-fused eight-membered ring containing sulfur. New reaction profile with sulfonium ylides.

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.

Unusual Ring-Expansion Reaction of Polyfluorinated Norbornenoxetanes

Synthesis ◽  
2007 ◽  
Vol 2007 (9) ◽  
pp. 1349-1354 ◽  
Author(s):  
Viacheslav Petrov ◽  
Will Marshall
Keyword(s):  
Ring Expansion ◽  
Ring Expansion Reaction
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