Bifunctional copper catalysts. A one step synthesis of bicyclic ethers starting from α,β-unsaturated ketones

Ravasio, Nicoletta; Leo, Vincenzo De; Babudri, Francesco; Gargano, M.

doi:10.1016/s0040-4039(97)01631-6

Cited by 14 publications

(3 citation statements)

References 10 publications

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“…We also reported that copper deposited on this kind of solids is an effective catalyst in bifunctional transformations such as intra- [3] and inter-molecular [4] ether formation starting from a ketone and an alcohol.…”

Section: Introductionmentioning

confidence: 90%

Mono and Bifunctional Catalysts for Styrene Oxide Isomerization or Hydrogenation

et al. 2011

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Section: Introductionmentioning

confidence: 90%

Mono and Bifunctional Catalysts for Styrene Oxide Isomerization or Hydrogenation

et al. 2011

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“…16 Excellent results were also obtained over these solid amorphous materials in the esterification of oleic acid with TMP. 17 We also succeeded several times in combining the acidic properties of these solids with the hydrogenation activity of prereduced CuO, both for the one step synthesis of ethers starting from ketones 18,19 and for the esterification and simultaneous hydrogenation of tall oil. In this case, the presence of Lewis acid sites was evident in the spectrum of adsorbed pyridine after deposition of the CuO phase on the acidic support.…”

Section: Communicationmentioning

confidence: 99%

New generation biofuels: γ-valerolactone into valeric esters in one pot

et al. 2013

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“…20 Thus, a feasible approach to prepare 1 could be based on the cyclization of dihydro-β-ionol (6) and dihydro-α-ionol (7), previously obtained from β-ionone (2) and α-ionone (3), respectively, by conventional functional groups interconversion (Scheme 1). Chlorosulfonic acid was chosen to perform both cyclizations, as it has been demonstrated to be a Table 1.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and odour evaluation of stereoisomers of octahydrobenzopyran derivatives

et al. 2006

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The synthesis and isolation of the four racemic 2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-2H-1-benzopyran stereoisomers from β β β β β -ionone and α α α α α -ionone is reported. It was based on the cyclization of dihydro-β β β β β -ionone and dihydro-α α α α α -ionone with chlorosulfonic acid at low temperature to yield stereospecifically the trans-fused and cis-fused hexahydrobenzopyran derivatives, respectively. The direct cyclization of dihydro-β β β β β -ionol and dihydro-α α α α α -ionol under identical conditions was also explored. In addition to the complete spectroscopic characterization of every isolated isomer, a description of their olfactory properties is displayed. ExperimentalReactions were monitored by gas chromatography (GC) on a Varian CP-3800 gas chromatograph fitted with a methyl silicone (CP-Sil 8 CB) capillary column (30 m × 0.25 mm i.d., film thickness 0.25 µm); carrier gas, He; flow rate, 1 mL/min; oven temperature programme, 50-290°C at a rate of 8°C/min; injector temperature, 250°C; flame ionization detector temperature, 300°C; retention times (R t ) are expressed in minutes; retention indices ( RI) referred to n-alkanes, determined on a DB-5 typephase capillary column according to reference 16. The reaction products were purified by conventional column chromatography (Merck silica gel 60, 70 -230 mesh) or by flash chromatography (Scharlau silica gel 60, 230-240 mesh), in both cases using appropriate mixtures of hexane and Et 2 O.

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Bifunctional copper catalysts. A one step synthesis of bicyclic ethers starting from α,β-unsaturated ketones

Cited by 14 publications

References 10 publications

Mono and Bifunctional Catalysts for Styrene Oxide Isomerization or Hydrogenation

Mono and Bifunctional Catalysts for Styrene Oxide Isomerization or Hydrogenation

New generation biofuels: γ-valerolactone into valeric esters in one pot

Synthesis and odour evaluation of stereoisomers of octahydrobenzopyran derivatives

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