A highly selective method for the synthesis of phenylacetaldehyde

Paparatto, G.; Gregorio, Gilbert F. De

doi:10.1016/s0040-4039(00)80328-7

Cited by 27 publications

(7 citation statements)

References 6 publications

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“…The DODH of such terminal aliphatic glycols is regiospecific, forming the terminal olefin (≥99%) exclusively (entries 8–20). Besides the alkene, variable amounts of minor byproduct, primarily ethers and phenylacetaldehyde, derived from acid-promoted alcohol dehydration and rearrangement, were detectable by GC, GC-MS, and NMR analysis of the reaction mixtures.…”

Section: Resultsmentioning

confidence: 99%

Sulfite-Driven, Oxorhenium-Catalyzed Deoxydehydration of Glycols

2011

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Methyltrioxorhenium and perrhennate salts catalyze the deoxydehydration (DODH) of glycols by sulfite, producing olefins regiospecifically. The scope and efficiency of these reactions with respect to the polyol substrate, reducing agent, catalyst, solvents, and various additives are investigated. In general, MeReO3 is a more active catalyst for sulfite-driven DODH, but the Z+ReO4 – derivatives (Z = Na, Bu4N) are more selective. Epoxides are also deoxygenated by Na2SO3/MeReO3, but not by Bu4NReO4. The perrhenate catalysts also promote glycol DODH with other reductants, e.g., PR3, secondary alcohols, and ArSMe. The DODH reactions of 1,2-cyclohexanediol and (+)-diethyl tartrate occur with high syn-stereoselectivity. The polyol meso-erythritol is largely converted to 1,3-butadiene with minor amounts of 2-butene-1,4-diol and 2,5-dihydrofuran, indicating faster terminal glycol DODH. Stoichiometric reaction studies demonstrate the viability of a catalytic pathway involving (a) glycol condensation with MeReO3 to form MeReVIIO2(glycolate); (b) O-transfer reduction of the ReVII-glycolate by sulfite or PR3 to produce [MeRevO(glycolate)]2; and (c) thermal fragmentation of the reduced Re-glycolates to produce olefin (and regeneration of MeReO3).

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Section: Resultsmentioning

confidence: 99%

Sulfite-Driven, Oxorhenium-Catalyzed Deoxydehydration of Glycols

2011

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“…As previously reported, this reaction can be easily accomplished in the presence of Brönsted and Lewis acids [67] or bases [68]. Porous materials, such as zeolites, with moderate-strong acid sites [69][70][71] and amorphous silica-alumina having weak-moderate acid sites [72,73] have been used as effective acid catalysts for styrene oxide isomerization in liquid and gas phase.…”

Section: Isomerization Of Styrene Oxidementioning

confidence: 86%

Effect of aluminium incorporation by the “pH-adjusting” method on the structural, acidic and catalytic properties of mesoporous SBA-15

Ungureanu

Drăgoi

Hulea

et al. 2012

Microporous and Mesoporous Materials

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“…These systems include Brφnsted or Lewis acids [177][178][179][180] give a good yield of phenylacetaldehyde [190][191][192][193]. Also, rearrangements of different epoxides over acidic zeolites at 200-300 °C have been reported [194].…”

Section: Rearrangement Of Aromatic Epoxidesmentioning

confidence: 99%