Kinetics and Products of the Acid-Catalyzed Ring-Opening of Atmospherically Relevant Butyl Epoxy Alcohols

2010 ◽  
Vol 114 (31) ◽  
pp. 8106-8113 ◽  
Author(s):  
Nathan C. Eddingsaas ◽  
David G. VanderVelde ◽  
Paul O. Wennberg
Keyword(s):  
Ring Opening ◽  
Acid Catalyzed ◽  
Epoxy Alcohols ◽  
Atmospherically Relevant

Borinic Acid-Catalyzed, Regioselective Ring Opening of 3,4-Epoxy Alcohols

2018 ◽  
Vol 20 (17) ◽  
pp. 5375-5379 ◽  
Author(s):  
Grace Wang ◽  
Graham E. Garrett ◽  
Mark S. Taylor
Keyword(s):  
Ring Opening ◽  
Acid Catalyzed ◽  
Epoxy Alcohols ◽  
Borinic Acid

scholarly journals Influence of the Substituents on the Opening of Silylepoxy Alcohols: 5-exo-Cyclization towards Tetrahydrofurans vs. Unexpected Side Reaction Leading to Tetrahydropyrans

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7386
Author(s):  
Carlos Díez-Poza ◽  
Asunción Barbero
Keyword(s):  
Ring Opening ◽  
Side Reaction ◽  
Structural Factors ◽  
Reaction Conditions ◽  
Effect Of Substituents ◽  
Different Types ◽  
Acid Catalyzed ◽  
Epoxy Alcohols

The regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The 5-exo opening being preferred vs. the 6-endo mode, according to Baldwin rules, the use of silyl-substituted oxiranes has been reported as a possible method to favor the 6-endo cyclization. However, there is a need for a detailed study on the different factors (structural factors, catalyst nature or conditions) that influence this process. In this paper, the acid-catalyzed cyclization of epoxysilyl alcohols was studied, focusing on the effect of substituents and reaction conditions on the outcome of the process. Two types of heterocycles (tetrahydrofurans or tetrahydropyrans) were selectively obtained depending on the structure of the initial epoxysilyl alcohol. Interestingly, cyclization of hindered epoxysilyl alcohols mainly proceeds through an unexpected side reaction, which implies a previous isomerization to an aldehyde. A mechanistic proposal for the formation of the different products is presented.

ChemInform Abstract: NEIGHBORING GROUP EFFECTS IN EPOXIDE RING OPENING, CIS-EPOXY-ALCOHOLS

1976 ◽  
Vol 7 (42) ◽  
pp. no-no
Author(s):  
ERWIN GLOTTER ◽  
PNINA KRINSKY ◽  
MIRIAM REJTOE ◽  
MARTIN WEISSENBERG
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Neighboring Group ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects
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