Title : ( Highly selective conversion of 1◦ and 2◦ tetrahydropyranyethers to thiocyanates and 3◦ ones to isothiocyanates usingltriphenylphosphine/diethyl azodicarboxylate/NH4SCN )
Authors: Batool Akhlaghinia ,
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Abstract
An efficient and selective method is described for the conversion of 1◦ and 2◦ tetrahydropyranyl (THP) ethers to their corresponding thiocyanates and 3◦ ones to isothiocyanates using a triphenylphosphine/diethyl azodicarboxylate (DEAD)/NH4SCN reagent system. This system is highly selective for thiocyanation of 1◦ THP-ethers in the presence of 2◦ and 3◦ ones and also 2◦ THP-ethers in the presence of a 3◦ analog. With this selective method, alcohols and trimethylsilyl ethers react, while THP-ethers remained intact in the presence of alcohols and trimethylsilyl ethers.
Keywords
Triphenylphosphine (PPh3); Diethyl azodicarboxylate (DEAD); Thiocyanation; Tetrahydropyranyl ether
@article{paperid:1008763,
author = {Akhlaghinia, Batool},
title = {Highly selective conversion of 1◦ and 2◦ tetrahydropyranyethers to thiocyanates and 3◦ ones to isothiocyanates usingltriphenylphosphine/diethyl azodicarboxylate/NH4SCN},
journal = {Synthesis},
year = {2005},
month = {February},
issn = {0039-7881},
keywords = {Triphenylphosphine (PPh3); Diethyl azodicarboxylate (DEAD); Thiocyanation;
Tetrahydropyranyl ether},
}
%0 Journal Article
%T Highly selective conversion of 1◦ and 2◦ tetrahydropyranyethers to thiocyanates and 3◦ ones to isothiocyanates usingltriphenylphosphine/diethyl azodicarboxylate/NH4SCN
%A Akhlaghinia, Batool
%J Synthesis
%@ 0039-7881
%D 2005
