40698-67-7Relevant academic research and scientific papers
Highly efficient synthesis of 1,3-dioxanes via prins reaction in bronsted-acidic imidazolium ionic liquid
Kalkhambkar, Rajesh G.,Jeong, Yeon T.
, p. 762 - 771 (2014/03/21)
The high-yielding synthesis of a wide variety of 1,3-dioxanes via the Prins reaction under mild conditions has been demonstrated using Bronsted- acidic imidazolium ionic liquid [bmim(SO3H)][OTf] or bmimOTf. The use of ionic liquid makes this synthesis simple, convenient, cost-effective, and environmentally friendly. Furthermore, bmimOTf was conveniently separated from the products and can be easily recycled for the Prins reaction with excellent yields. This method works well with a variety of aliphatic aldehydes including formaldehyde, acetaldehyde, propionaldehyde, and cyclohexanecarboxaldehyde. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Iodine as a mild and versatile reagent for the synthesis of 1,3-dioxane derivatives via the Prins reaction
Yadav,Reddy, B.V. Subba,Hara Gopal,Narayana Kumar,Madavi,Kunwar
, p. 4420 - 4423 (2008/12/21)
Iodine is found to be an effective reagent for the cross-coupling of olefins with aldehydes under mild conditions to produce 4-substituted 1,3-dioxane derivatives in excellent yields and in short reaction times with high selectivity. The use of iodine makes this procedure simple, convenient, cost-effective and practical. This method works not only with formaldehyde but also with acetaldehyde, propionaldehyde and cyclohexanecarboxaldehyde.
Cation-Exchanged Montmorillonite (Mn+-Mont)-Catalyzed Prins Reaction
Tateiwa, Jun-Ichi,Hashimoto, Keiji,Yamauchi, Takayoshi,Uemura, Sakae
, p. 2361 - 2368 (2007/10/03)
The Prins reaction of styrenes with paraformaldehyde or 1,3,5-trioxane in toluene in the presence of cation-exchanged montmorillonite (Mn+-mont), which worked as a Bronsted acid catalyst, at 80°C produced 4-aryl-1,3-dioxanes selectively in up to 99% isolated yield with a turnover number of up to 5.9×102. Among the examined 21 Mn+-monts, Ce3+- and Fe3+-monts were revealed to be quite effective. Regeneration of the catalyst was confirmed with the Ce3+-mont, which could be effectively recycled at least three times. Many lanthanide metal ion-exchanged montmorillonites (Ln3+-monts) were prepared and characterized by X-ray powder diffraction (XRD) and temperature-programmed desorption of ammonia gas (NH3-TPD) methods.
CONDENSATION D'ALCENES AROMATIQUES AVEC L'ACETALDEHYDE CATALYSEE PAR DES RESINES ECHANGEUSES D'IONS-II; STEREOISOMERISATION ET SYNTHESE DE NOUVEAUX DIOXA-1,3 CYCLOHEXANES POLYSUBSTITUES
Gharbi, R. El,Delmas, M.,Gaset, A.
, p. 2953 - 2964 (2007/10/02)
The interconversion of the three stereoisomers of 4-anisyl-2,5,6 trimethyl-1,3 dioxacyclohexane, obtained from the condensation reaction between anethole and acetaldehyde, depends on the experimental conditions.In some cases, a reversal to the starting alkene could be observed: such a phenomenon does not seem to have been reported so far in the isomerization reactions of 1,3-dioxacyclohexanes.The data can be accounted for by a reaction mechanism involving various cationic intermediates.New 1,3-dioxacyclohexanes were obtained from acetaldehyde and various aromatic alkenes under mild reaction conditions in the presence of sulfonic ion-ex changers used as catalysts, in good yields and with high selectivity.
