A nuclear magnetic resonance kinetic study of the acid-catalyzed epoxide ring opening of tetramethylethylene oxide

1978 ◽  
Vol 100 (10) ◽  
pp. 3122-3127 ◽  
Author(s):  
Y. Pocker ◽  
B. P. Ronald
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Kinetic Study ◽  
Ring Opening ◽  
Epoxide Ring ◽  
Epoxide Ring Opening ◽  
Acid Catalyzed ◽  
Nuclear Magnetic

Reaction of glyoxal at the ortho position of phenols. Synthesis of 5a,10b-dihydrobenzofuro[2,3-b]benzofurans and 2-(3-benzofuranyl)phenols

1967 ◽  
Vol 45 (15) ◽  
pp. 1777-1784 ◽  
Author(s):  
E. C. M. Coxworth
Keyword(s):  
Molecular Weight ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Ortho Position ◽  
Acidic Media ◽  
Nuclear Magnetic Resonance Spectra ◽  
Acid Catalyzed ◽  
Magnetic Resonance Spectra ◽  
Nuclear Magnetic

The acid-catalyzed reaction of glyoxal at the ortho position of phenols has been shown to yield, as initial products, substituted 5a,10b-dihydrobenzofuro[2,3-b]benzofurans, such structures being indicated by the nuclear magnetic resonance spectra, and confirmed in several cases by synthesis via an unambiguous route. At higher temperatures in acidic media, and in the absence of glyoxal, these initial products were converted into the corresponding 2-(3-benzofuranyl)phenols. When glyoxal was present in acidic media, the 2-(3-benzofuranyl)phenols reacted further to give unidentified products of appreciably higher molecular weight.

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