Publication

Unexpected Selectivity between Pinacolic Rearrangement and Intramolecular Displacement in the Acid-Promoted Epoxide Ring-Opening of 6-Exo-Cyano-3,8-Dioxabicyclo[3.2.1.0(2,4)]Oct-6-Endo-Yl Esters

Pierre Vogel
1994
Journal Articles

Abstract

Acid promoted epoxide ring opening of 2-exo-cyano-5-exo,6-exo-epohy-7-oxa-bicyclo[2.2.1]hept-2-endo-yl acetate is accompanied by a Wagnet-Meerwein (pinacolic) rearrangemant when run in CH2Cl2/HSO3-F and by endo acetoxy group participation when run in CF3CH(OH)CF3/HClO4. An efficient and stereoselective trans-double hydroxylation of centers C(5) and C(6) of the ''naked sugar'' (1R,2S,4R)-2-exo-cyano-7-oxabicyclo[2.2.1]hept-2-endo-yl (1S')-camphanate is also presented.

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Pierre Vogel
1994
Journal Articles

Abstract

Official source

Related concepts (6)

Chlorine

Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

Chloride

The term chloride refers either to a chloride ion (), which is a negatively charged chlorine atom, or a non-charged chlorine atom covalently bonded to the rest of the molecule by a single bond (). Many inorganic chlorides are salts. Many organic compounds are chlorides. The pronunciation of the word "chloride" is ˈklɔəraɪd. The chloride ion is an anion (negatively charged ion) with the charge Cl-. Chloride salts such as sodium chloride are often soluble in water.

Ether

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers.