40559-74-8Relevant articles and documents
Al(HSO4)3/silica gel as a novel catalytic system for the ring opening of epoxides with thiocyanate anion under solvent-free conditions
Kiasat, Ali Reza,Mouradzadegun, Arash,Elahi, Somayeh,Fallah-Mehrjardi, Mehdi
, p. 146 - 150 (2010)
For the first time, metal hydrogen sulfates and phosphates/silica gel have been studied as efficient and powerful solid acid catalysts in the ring opening of epoxides with thiocyanate anion. The most significant result was obtained by Al(HSO4)3/SiO2 which afforded the corresponding β-hydroxy thiocyanates under mild reaction conditions and in very short reaction times. The cheapness, availability of the catalyst, ease of procedure and work-up make this method attractive for the organic synthesis.
DDQ catalyses the conversion of epoxides to β-hydroxy thiocyanates with NH4SCN
Iranpoor, Nasser,Kohmareh, Gholam Ali
, p. 135 - 139 (1999)
2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) catalyses the addition of thiocyante ion to epoxides to afford β-hydroxy thiocyanates in high yields and regioselectivity.
Schiff-base metal(II) complexes as new catalysts in the efficient, mild and regioselective conversion of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanate
Sharghi, Hashem,Nasseri, Mohammad Ali
, p. 137 - 142 (2003)
A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of some Schiff-base complexes of metal(II) is described. The cleavage of the oxirane ring is found to proceed regioselectively under mild reaction conditions. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.
Melamine sulfonic acid: A recoverable catalyst for the ecofriendly synthesis of thiocyanohydrins under solvent-free conditions
Kiasat, Ali Reza,Fallah-Mehrjardi, Mehdi
, p. 1551 - 1558 (2010)
Melamine sulfonic acid as a novel and efficient solid acid catalyst has been synthesized and used in the ring opening of epoxides under solvent-free conditions. This catalyst afforded the corresponding thiocyanohydrins with good regioselectivity and very short reaction times. The catalyst can be easily separated and reused several times without appreciable loss of activity. The availability and recoverability of the catalyst with easy operation and workup make this method attractive for organic synthesis. Copyright Taylor & Francis Group, LLC.
Synthesis of thiocyanohydrins from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid-liquid phase-transfer catalyst
Tamami, Bahman,Mahdavi, Hossein
, p. 6225 - 6228 (2002)
Poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride resin was developed as a new polymeric phase-transfer catalyst. This quaternized polyacrylamide catalyzed the regioselective ring opening of epoxides by thiocyanate ion to give thiocyanohydrins in high yields under mild conditions.
Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate
Andreev, Ivan A.,Ratmanova, Nina K.,Augustin, André U.,Ivanova, Olga A.,Levina, Irina I.,Khrustalev, Victor N.,Werz, Daniel B.,Trushkov, Igor V.
supporting information, p. 7927 - 7934 (2021/03/03)
We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Br?nsted acid inducing diverse transformations via general acid catalysis, and c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, respectively, in a single time-efficient step. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations.
Fe3O4 nanoparticle-bonded β-cyclodextrin as an efficient and magnetically retrievable catalyst for the preparation of β-azido alcohols and β-hydroxy thiocyanate
Sayyahi, Soheil,Mozafari, Sara,Saghanezhad, Seyyed Jafar
, p. 511 - 518 (2016/04/26)
A novel Fe3O4 nanoparticle-bonded β-cyclodextrin (β-CD@MNP) has been synthesized and characterized by scanning electron microscopy, vibrating sample magnetometry, and thermogravimetric analysis. It is found that the nanoparticles can
