22564-83-6Relevant academic research and scientific papers
Use of metal-accumulating plants for implementing chemical reactions
-
Page/Page column 38-40, (2015/10/28)
The use of metal-accumulating plants for implementing chemical reactions.
The Hendrickson reagent and the Mitsunobu reaction: A mechanistic study
Elson, Kathryn E.,Jenkins, Ian D.,Loughlin, Wendy A.
, p. 2958 - 2965 (2007/10/03)
The alkoxytriphenylphosphonium ion intermediate of the Mitsunobu reaction can be generated using the Hendrickson reagent, triphenylphosphonium anhydride trifluoromethanesulfonate, 1. Strangely, while the reagent 1 can be used in place of the Mitsunobu reagents (triphenylphosphine and a dialkylazodicarboxylate) for the esterification of primary alcohols, secondary alcohols such as menthol undergo elimination. Evidence is presented to show that this unexpected result is due to the presence of trialkylammonium triflate salts. Such salts lead to a dramatic decrease in the rate of esterification relative to competing elimination. The Mitsunobu esterification of menthol with p-nitrobenzoic acid was re-examined and the occurrence of elimination reported for the first time. The presence of traces of tetrabutylammonium triflate led to a dramatic reduction in the yield of inverted ester and a corresponding increase in the yield of anti elimination product 2-menthene. The mechanism of the Mitsunobu reaction is discussed in the light of the dramatic salt effect on both the rate and outcome of the reaction and the possible involvement of ion pair clustering. In contrast, use of the reagent 1 resulted in syn elimination to give a 1:2 mixture of 2- and 3-menthenes. Finally, 1 and sodium azide can be used to convert a primary alcohol into an azide in high yield. There was no reaction under Mitsunobu conditions.
Dehydration of Alcohols Catalysed by Heteropolyacids Supported on Silica
Alesso, Elba,Torviso, Rosario,Finkielsztein, Liliana,Lantano, Beatriz,Moltrasio, Graciela,Aguirre, Jose,Vazquez, Patricia,Pizzio, Luis,Caceres, Carmen,Blanco, Mirta,Thomas, Horacio
, p. 1232 - 1245 (2007/10/03)
Keggin type heteropolyacids supported on silica efficiently dehydrate secondary and tertiary alcohols under mild conditions and in good yields to afford the correspondent alkenes.
