Oxiranes from methylenation of the ester carbonyl group by diazomethane

1988 ◽  
Vol 53 (14) ◽  
pp. 3321-3325 ◽  
Author(s):  
Paolo Strazzolini ◽  
Giancarlo Verardo ◽  
Angelo G. Giumanini
Keyword(s):  
Carbonyl Group ◽  
Ester Carbonyl ◽  
Ester Carbonyl Group

ChemInform Abstract: Carbon-Carbon Bond Formation Between Enone and Ester Carbonyl Group Induced by Samarium Diiodide.

ChemInform ◽  
2009 ◽  
Vol 40 (10) ◽  
Author(s):  
Masakazu Sono ◽  
Takayuki Mizutani ◽  
Masayo Nozaki ◽  
Shigeru Takaoka ◽  
Motoo Tori
Keyword(s):  
Carbonyl Group ◽  
Bond Formation ◽  
Samarium Diiodide ◽  
Carbon Bond ◽  
Ester Carbonyl ◽  
Ester Carbonyl Group ◽  
Carbon Carbon Bond

Positional selectivity of the methylation of 5-substituted tetrazolate anions

1984 ◽  
Vol 37 (12) ◽  
pp. 2453 ◽  
Author(s):  
RJ Spear
Keyword(s):  
Carbonyl Group ◽  
Reaction Pathway ◽  
Steric Effects ◽  
Ester Carbonyl ◽  
Ester Carbonyl Group ◽  
Acetone Water ◽  
Positional Selectivity ◽  
Electro Negativity ◽  
Electronic And Steric Effects

The methylation of a series of 15 sodium 5-substituted tetrazolates using iodomethane in acetone/water (4 : 1) has been studied. The reaction yields both 1- and 2-methyl products, and the ratio of these products is discussed in terms of the nature of the 5-substituent. Electronic and steric effects dominate the reaction pathway; both increased substituent electro negativity and steric bulk lead to predominant methylation at N2. Sodium 5-ethoxycarbonyltetrazolate (3n) goes against this trend and an intermediate is proposed where the incoming electrophile is associated with the ester carbonyl group.

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