85250-56-2Relevant articles and documents
Direct synthesis of allyl sulfides from allyl alcohols and thiols
Tsay,Lin,Furth,Shum,King,Yu,Chen,Hwu
, p. 329 - 334 (2007/10/02)
In the presence of boron trifluoride-diethyl ether complex, various allyl alcohols [(-)-myrtenol, geraniol, cinnamyl alcohol, linalool, 1-octen-3-ol, 2-hydroxybenzyl alcohol and bicyclic diols] were reacted with thiophenol, 1-butanethiol, trimethyl(phenylthio)silane or hexamethylsilane in dichloromethane at room temperature to give the corresponding allyl sulfides in good to excellent yields. The mild conditions for this transformation allowed chemoselectivity.
The use of metal reagents in stereo- and regioselective functionalizations of conjugated dienes
Baeckval, Jan-E
, p. 665 - 670 (2007/10/02)
Conjugated dienes have been selectively functionalized via 1-acetoxy-4-chloro-2-alkenes and via 2-(phenylsulfonyl)-1,3-dienes.In both these approaches nucleophiles can be added to the 1- and 4-positions.It was shown that also non-stabilized carbon nucleophiles (from cuprates or copper(I)-catalyzed Grignard reactions) can be used.The utility of the functionalizations was demonstrated by the syntheses of a marine natural product and a butterfly pheromone.Finally, the 2-(phenyl-sulfonyl)-1,3-dienes show a dual electron demand in Diels-Alder reactions and give cycloadducts with both electron-rich and electron-deficient olefins.
A Dual Regiocontrol in the Copper-catalysed Grignard Reaction with Primary Allylic Acetates
Baeckvall, Jan-E.,Sellen, Michael
, p. 827 - 829 (2007/10/02)
The reaction of primary allylic acetates with Grignard reagents in the presence of catalytic amounts of Li2CuCl4 can be regiochemically controlled to give either α- or γ-substitution of the allylic acetoxy group.