Naslov
Successive Cleavage of Allylic Ethers by Polysulfone

Autori
Dean Marković, Peter Steunenberg and Pierre Vogel

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Chimia / - , 2003, 270-270

Skup
Swiss Chemical Society Meeting

Mjesto i datum
Zürich, Švicarska, 17.09.2003

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
protecting groups, green chemistry, deprotection

Sažetak
Polysulfones (copoly1ners of alkene and 802) are capable to is01nerise alkenes. The process itnplies the formation of an initial ally! radical, formed by a chain-process involving the hydrogen transfer between the alkene and the intennediate ally! radical. The fonnation of the latter intennediate is two steep process in which a RS02· radical abstracts first an electron from the alkene with formation of an radical cation. In the second steep the latter loses a proton with fonnation of an allyl radical. Accordingly, the rate of the polysulfone catalysed alkene isomerisation depends strongly upon its ionisation potential. This fact has been used to invent a new strategy for alcohol, aldehyde, ketone and he1niacetal protections. While allyl ethers are not isomerised with polysulfone, 1netahallyl ethers are iso1nerised into the corresponding encl ethers (and then hydrolysed) on heating with polysulfone catalyst. Prenyl ethers and methylprenyl ethers are iso1nerised much faster. A polyol protected as allyl, 1netallyl and methylprenyl ethers will be deprotected under neutral conditions by the polysulfone with the following reaction sequence,

Izvorni jezik
Engleski

POVEZANOST RADA