135907-99-2Relevant articles and documents
Simple synthesis of β-acetoxy thiocyanates from oxiranes
Lukowska-Chojnacka, Edyta,Plenkiewicz, Jan
experimental part, p. 1999 - 2006 (2011/06/24)
A convenient and simple method for the preparation of previously unknown β-acetoxy thiocyanates by regioselective ring opening of the corresponding oxiranes with thiocyanate anion followed by acetylation is described. The shorter reaction times, better yields of the products, and easy workup are the advantages of this methodology.
β,γ-EPOXY SULFONES IN ORGANIC SYNTHESIS. PART 2: PREPARATION OF β,γ-BIFUNCIONALIZED SULFONES
Najera, Carmen,Sansano, Jose M.
, p. 5193 - 5202 (2007/10/02)
Heteronucleophiles reagents react with β,γ-epoxy sulfones 1 at the γ position in the presence of Ti(OPri)4 or magnesium halides to afford regioselectively γ-functionalized β-hydroxy sulfones 2.With soft nucleophiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids.In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the β-functionalized γ-hydroxy sulfones 3 were exclusively obtained.The preparation of compounds 3 (R2 = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Michael addition of different heteronucleophiles.