878-57-9Relevant academic research and scientific papers
Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions
Smith, Brendan M.,Kubczyk, Tomasz M.,Graham, Andrew E.
experimental part, p. 7775 - 7781 (2012/09/21)
Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf)3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.
An efficient photoinduced deprotection of aromatic acetals and ketals
Thevenet, Damien,Neier, Reinhard
, p. 331 - 346 (2011/04/22)
A novel type of photodeprotection reaction of simple aromatic acetals and ketals is described. The deprotection is highly efficient under optimized conditions. The aromatic ring confers the photoreactivity to the compounds. The efficiency of the process depends on the structure of the acetal moiety. The common minor side reaction, the photooxidation, becomes the major reaction pathway in the cases of cyclic acetals. The use of photon as only reagent makes this procedure especially attractive for acetal deprotection.
Acetalization of carbonyl compounds catalyzed by bismuth triflate under solvent-free conditions
Aliyan, Hamid,Fazaeli, Razieh,Massah, Ahmad Reza,Momeni, Ahmad Reza,Naghash, Hamid Javaherian,Moeinifard, Behzad
experimental part, p. 873 - 876 (2012/04/05)
Carbonyl compounds were converted to the corresponding 1,3-dioxolanes and 1,3-dioxanes with ethylene glycol and 1,3-propandiol in the presence of bismuth triflate under solvent-free conditions. In addition, high chemoselective protection of aldehydes in the presence of ketones has been achieved.
Highly efficient and chemoselective acetalization of carbonyl compounds catalyzed by new and reusab e zirconyl triflate, zr0(0tf)2
Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yazdani, Parvin,Ghorjipoor, Saeedeh
experimental part, p. 131 - 135 (2009/09/30)
Various types of aromatic aldehydes were efficiently converted to their corresponding 1,3-dioxanes and 1,3-dioxolane with 1,3-propanediol and ethylene glycol, respectively, in the presence of catalytic amount of ZrO(OTf) 2 in acetonitrile at room temperature. The catalyst can be reused several times without loss of its catalytic activity. Very short reaction times, selective acetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones, very mild reaction conditions, reusability of the catalyst, and easy workup are noteworthy advantages of this method.
Regioselective transformation of alkynes into cyclic acetals and thioacetals with a gold(I) catalyst: comparison with Br?nsted acid catalysts
Santos, Laura L.,Ruiz, Violeta R.,Sabater, Maria J.,Corma, Avelino
, p. 7902 - 7909 (2008/12/21)
Au(I) catalyzes the transformation of alkynes into cyclic acetals and thioacetals at much higher rate than Br?nsted acids. The reaction appears to be general for a range of alkynes and diols or dithiols, which are efficiently transformed with high selectivities. One of the salient features of this reaction process is the high reactivity of the enol ether or enol thioether intermediates, which undergo a rapid isomerization reaction to afford the cyclic acetals or thioacetals, so that isolation or subsequent activation processes are not required. This type of reactions allows us to synthesize a series of fragrances.
N-bromosuccinimide (NBS) catalyzed highly chemoselective acetalization of carbonyl compounds using silylated diols and pentaerythritol under neutral aprotic conditions
Karimi, Babak,Hazarkhani, Hassan,Maleki, Jafar
, p. 279 - 285 (2007/10/03)
Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes and pentaerythritol diacetals by the use of either 1,3-bistrimethylsiloxy propane (A) or 1,3-bistrimethylsilanyloxy-2,2- bistrimethylsilanyloxymethyl propane (D) and a catalytic amount of N-bromosuccinimide (3-10 mol%) under essentially neutral aprotic condition, respectively. A variety of functionalities such as both aliphatic and phenolic -OTBDMS, -OMe, -OBz, furan ring, double bonds and more significantly phenolic -OTHP survived under the present reaction condition. The efficient conversion of two α-tertiary ketones to their cyclic acetals was also achieved using the present protocol.
Highly efficient and chemoselective interchange of 1,3-oxathioacetals and dithioacetals to acetals promoted by N-halosuccinimide
Karimi, Babak,Seradj, Hassan,Maleki, Jafar
, p. 4513 - 4516 (2007/10/03)
Highly efficient interconversion of a range of 1,3-oxathiolanes, 1,3-dithiolanes and 1,3-dithianes to their acetals at ambient temperature using N-bromosuccinimide or N-chlorosuccinimide and different types of alcohols and diols was investigated.
Iodine-catalyzed, efficient and mild procedure for highly chemoselective acetalization of carbonyl compounds under neutral aprotic conditions
Karimi, Babak,Golshani, Behzad
, p. 784 - 788 (2007/10/03)
Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes by the use of 1,3-bis(trimethylsiloxy)propane (BTSP) and a catalytic amount of iodine (3-7 mol%) under essentially neutral aprotic condition.
Tetrabutylammonium tribromide (TBATB) as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds
Gopinath, Rangam,Haque, Sk. Jiaul,Patel, Bhisma K.
, p. 5842 - 5845 (2007/10/03)
Acyclic and cyclic acetals of various carbonyl compounds were obtained in excellent yields under a mild reaction condition in the presence of trialkyl orthoformate and a catalytic amount of tetrabutylammonium tribromide (TBATB) in absolute alcohol. Chemoselective acetalization of an aldehyde in the presence of ketone, unsymmetrical acetal formation, shorter reaction times, mild reaction conditions, the stability of acid-sensitive protecting groups, high efficiencies, facile isolation of the desired products, and the catalytic nature of the reagent make the present methodology a practical alternative.
An efficient procedure for the preparation of cyclic ketals and thioketals catalyzed by zirconium sulfophenyl phosphonate
Curini,Epifano,Marcotullio,Rosati
, p. 1182 - 1184 (2007/10/03)
A convenient method for the preparation of cyclic ketals and thioketals using zirconium sulfophenyl phosphonate as catalyst is described.
