New aspects of the telluroxide elimination. A facile elimination of sec-alkyl phenyl telluroxide leading to olefins, allylic alcohols, and allylic ethers

Journal Article · Wed May 04 00:00:00 EDT 1983 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00347a039· OSTI ID:5626689

Uemura, S; Fukuzawa, S

The utility of the telluroxide for olefin synthesis, a reaction which previously appeared to be of little value is described. Treatment of sec-alkylphenyltellurium dibromides, except for the cyclohexyl system, with aqueous NaOH at room temperature affords olefins, allylic alcohols, and/or allylic ethers in high yields presumably via the formation of sec-alkyl phenyl telluroxides and their facile telluroxide elimination. As to the formation of linear olefins, more preference for elimination toward the less substituted carbon was observed than the selenoxide and sulfoxide eliminations. In the cyclododecyl case only trans-cyclododecene was formed as an olefin componenet in a sharp constrast to the selenoxide elimination that affords a 1:1 mixture of cis and trans isomers. On the contrary, in the n-alkyl and cyclohexyl cases the corresponding telluroxides are stable compounds that afford similar elimination products including vinylic ethers only by neat pyrolysis at temperatures above 200/sup 0/C.

• Research Organization: Kyoto Univ., Japan
• OSTI ID: 5626689
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 105:9
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALKENES
CHEMICAL PREPARATION
TELLURIUM COMPOUNDS
CHEMICAL REACTIONS
ALCOHOLS
BROMIDES
ETHERS
ORGANIC COMPOUNDS
OXIDES
BROMINE COMPOUNDS
CHALCOGENIDES
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
SYNTHESIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
400201 - Chemical & Physicochemical Properties