5182-36-5Relevant academic research and scientific papers
Prins cyclization of styrenes or acetophenone catalyzed by DBSA in water
Zhang, Juan,Hua, Lin,Li, Feifei,Wu, Xuefen,Tian, Shengzhi,Yang, Jing
experimental part, p. 1234 - 1242 (2012/04/04)
Dodecylbenzenesulfonic acid (DBSA) was proved to be an efficient catalyst for Prins cyclization of styrenes and formaldehyde or acetaldehyde in water. A tandem dehydration/ Prins cyclization reaction using a tertiary alcohol and formaldehyde as substrates proceeded very well by using DBSA as catalyst. Acetophenone, which is less reactive compared with styrene, can also react with formaldehyde when catalyzed by DBSA in water to afford 1,3-dioxan-5- ylphenylmethanone in good yield. Copyright Taylor & Francis Group, LLC.
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.
Recyclable hafnium(IV) bis(perfluorooctanesulfonyl)amide complex for catalytic Friedel-Crafts acylation and Prins reaction in fluorous biphase system
Hao, Xiuhua,Yoshida, Akihiro,Hoshi, Nobuto
, p. 1396 - 1401 (2008/09/18)
In fluorous biphase system, hafnium(IV) bis(perfluorooctanesulfonyl)amide complex (Hf[N(SO2C8F17)2]4) was found to be a highly reactive and recyclable Lewis acid catalyst for Friedel-Crafts acylation and Prins reaction at significantly low catalyst loadings (≤1 mol%). In these reactions, Hf[N(SO2C8F17)2]4 is selectively soluble in the lower fluorous phase and can be recovered simply by phase separation. Furthermore, the catalyst can be reused without decrease of activity.
Facile and recyclable method for the Prins reaction using hafnium(IV) bis(perfluorooctanesulfonyl)amides in fluorous biphase system
Hao, Xiuhua,Hoshi, Nobuto
, p. 1102 - 1103 (2007/10/03)
In fluorous biphase system, Hf[N(SO2C8F 17)2]4 has been found to be an efficient catalyst for the Prins reaction of α-methyl styrene with aldehydes at low catalytic loading. The reaction proceeds smoothly and affords the corresponding 1,3-dioxanes in good yields. The catalyst is selectively soluble in lower fluorous phase and can be recovered simply by phase separation. Furthermore, the recovered fluorous phase containing catalyst can be recycled 17 times with yields consistently above 80%. Copyright
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.
