Cathodic elimination of β-acetoxy phenyl sulfones in acetonitrile

Autor:	Hidemitsu Uno, Akira Kunugi, Yoshitsugu Sano
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Sulfonyl Trifluoromethyl Double bond General Chemical Engineering Polyene Medicinal chemistry Sulfone chemistry.chemical_compound chemistry Electrochemistry Organic chemistry Fluorocarbon Acetonitrile Aliphatic compound
Zdroj:	Electrochimica Acta. 46:1879-1890
ISSN:	0013-4686
DOI:	10.1016/s0013-4686(01)00443-1
Popis:	The synthesis of polyenes by electrolysis of β-acetoxy phenyl sulfones having some double bonds was studied in acetonitrile using a Hg pool cathode and a sacrificial Mg anode. Most unsaturated β-acetoxy phenyl sulfones were subject to the electroreductive elimination of both the acetoxy and the sulfonyl groups, but did not give the desired polyenes because of partial hydrogenation of double bonds. The electrolytic reduction of a β-acetoxy phenyl sulfone having a trifluoromethyl group at the β-position was subjected to such 1,2-elimination followed by reductive removal of all fluorine atoms to afford the corresponding unsaturated hydrocarbons, whereas β-acetoxy phenyl sulfones having a fluorine atom at the α-position gave the desired fluoro-olefins in high yields. All saturated β-acetoxy phenyl sulfones afforded the desired alkenes in high yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::efb191e7c43bf47cc5eecdc85675d8cd https://doi.org/10.1016/s0013-4686(01)00443-1 Zobrazit plný text záznamu Full Text from ScienceDirect