Metal(IV) phosphate catalysed retro-Prins reaction involving an oxetane intermediate

Al-Qallaf, Fawzia A. H.; Johnstone, R. A. W.; Liu, Jun-Yao; Lu, Lyan Ywan; Whittaker, D.

doi:10.1039/a901122f

Cited by 7 publications

(8 citation statements)

References 12 publications

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“…In the literature, some metal carbonates, phosphates, and sulfates have been used as supports to load metals [2]. From the examples on the catalytic applications of metal phosphate-based catalysts cited in the Introduction section [4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,…”

Section: Resultsmentioning

confidence: 99%

“…In a classic book written by Tanabe, Misono, Ono, and Hattori, metal phosphates are highlighted as a new family of solid acids showing some promising applications in heterogeneous catalysis [3]. Metal phosphates can be used as catalysts directly, for instance, in the partial oxidation of propane [4], oxidative dehydrogenation of isobutane to isobutene [5,6,7], oxidative dehydrogenation of ethylbenzene to styrene [8], dehydration of cyclohexanol and 1-methylcyclohexanol [9,10,11], retro-Prins reaction [12,13], terpene rearrangements [14], alkylation of anisole with alcohols [15], dehydrofluorination of CF 3 CH 3 into CF 2 CH 2 [16,17], hydrolysis of CCl 2 F 2 [18,19,20], decomposition of CF 4 [21,22], decomposition of CH 2 FCF 3 [23], decomposition of chlorobenzene [24], decomposition of SF 6 [25,26], and hydrolysis of NF 3 [27]. …”

Section: Introductionmentioning

confidence: 99%

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Metal Phosphate-Supported Pt Catalysts for CO Oxidation

et al. 2014

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Oxides (such as SiO2, TiO2, ZrO2, Al2O3, Fe2O3, CeO2) have often been used to prepare supported Pt catalysts for CO oxidation and other reactions, whereas metal phosphate-supported Pt catalysts for CO oxidation were rarely reported. Metal phosphates are a family of metal salts with high thermal stability and acid-base properties. Hydroxyapatite (Ca10(PO4)6(OH)2, denoted as Ca-P-O here) also has rich hydroxyls. Here we report a series of metal phosphate-supported Pt (Pt/M-P-O, M = Mg, Al, Ca, Fe, Co, Zn, La) catalysts for CO oxidation. Pt/Ca-P-O shows the highest activity. Relevant characterization was conducted using N2 adsorption-desorption, inductively coupled plasma (ICP) atomic emission spectroscopy, X-ray diffraction (XRD), transmission electron microscopy (TEM), CO2 temperature-programmed desorption (CO2-TPD), X-ray photoelectron spectroscopy (XPS), and H2 temperature-programmed reduction (H2-TPR). This work furnishes a new catalyst system for CO oxidation and other possible reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal Phosphate-Supported Pt Catalysts for CO Oxidation

et al. 2014

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“…35 As presumed in Scheme 1, isomerization of the cis a/b-ring system of 5 to a trans a/b-ring system was followed by hemiacetalization involving the C-3 hydroxy and C-10 formyl groups. Formate 5g then could be formed via a retro-Prins reaction 35 of the intermediate hemiacetal. (Other related mechanisms for this reaction are also possible).…”

Section: Resultsmentioning

confidence: 99%

“…The mechanism of the formation of 5g from 5 could be proposed based on the retro-Prins reaction. 35 As presumed in Scheme 1, isomerization of the cis a/b-ring system of 5 to a trans a/b-ring system was followed by hemiacetalization involving the C-3 hydroxy and C-10 formyl groups. Formate 5g then could be formed via a retro-Prins reaction 35 of the intermediate hemiacetal.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity

et al. 2016

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Three new (1–3) and two known (4 and 5) cytotoxic cardiac glycosides were isolated and characterized from a medicinal plant, Streblus asper, collected in Vietnam, with six new and one known derivatives (5a–5g) synthesized from (+)-strebloside (5). A preliminary structure-activity relationship study indicated that the C-19 formyl and C-5 and C-14 hydroxy groups and C-3 sugar unit play important roles in the mediation of the cytotoxicity of (+)-strebloside (5) against HT-29 human colon cancer cells. When evaluated in NCr nu/nu mice implanted intraperitoneally with hollow fibers facilitated with either MDA-MB-231 human breast or OVCAR3 human ovarian cancer cells, (+)-strebloside (5) showed significant cell growth inhibitory activity in both cases, in the dose range 5–30 mg/kg.

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“…Amorphous titanium phosphates showed some, though minor (7%), activity in the ester production from menthol and isovaleric acid in the liquid state [18]. 1,3-Diols refluxed in the presence of amorphous zirconium or titanium phosphate undergo a retro-Prins reaction yielding a cyclic ketone and ethene (though the main product is still the expected cyclic alkene) [19,20]. Potassium exchanged layered zirconium hydrogen phosphate was employed as a catalyst for the cyanosililation of carbonyl compounds [21].…”

Section: Introductionmentioning

confidence: 99%