- Diels-Alder reaction of myrcene with carbonyl containing dienophiles supported on silica gel under microwave irradiation
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Diels-Alder reactions of myrcene (7-methyl-3-methene-1,6-octadiene) with carbonyl containing dienophiles supported on silica gel under microwave irradiation have been studied.
- Oskooie, Hossein Abdi
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- The search for new odorants: Synthesis of animalic fragrant and musky/ambery compounds
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An overview of the recent research which allowed us to discover novel animalic odorants is presented. The new derivatives were prepared from readily available starting materials via easy reaction steps in good yields. They possess very different structures, such as bicyclic pentanols, glycolates, or tricyclic ketones, and all show interesting notes in the animalic fragrant family: from costus, leathery to ambery and musky scents, making them all attractive for different purposes.
- Plessis, Caroline
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p. 1517 - 1539
(2015/03/03)
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- Unsaturated aldehydes as alkene equivalents in the Diels-Alder reaction
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A one-pot procedure is described for using α,β-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-with-drawing substituents. In this way, the aldehyde group serves as a traceless control element to direct the cycloaddition reaction. The Diels-Alder reactions are performed in a diglyme solution in the presence of a catalytic amount of boron trifluoride etherate. Subsequent quenching of the Lewis acid, addition of 0.3% of [Rh(dppp)2Cl] and heating to reflux achieves the ensuing decarbonylation to afford the product cyclohexenes. Under these conditions, acrolein, crotonaldehyde and cinnamaldehyde have been reacted with a variety of 1,3-dienes to afford cyclohexenes in overall yields between 53 and 88%. In these transformations, the three aldehydes serve as equivalents of ethylene, propylene and styrene, respectively.
- Taarning, Esben,Madsen, Robert
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supporting information; experimental part
p. 5638 - 5644
(2009/05/30)
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- High regioselective Diels-Alder reaction of myrcene with acrolein catalyzed by zinc-containing ionic liquids
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The ambient zinc-containing ionic liquids, MX-ZnCl2, functioning as both Lewis acid catalyst and green solvent, are employed for a high regioselective Diels-Alder reaction of myrcene with acrolein for the first time, where MX is either 1-butyl-3-methylimidazolium chloride (BmimCl), 1-ethyl-3-methylimidazolium bromide (EmimBr), N-butylpyridinium bromide (BPyBr), or N-ethylpyridinium bromide (EtPyBr). Compared with the analogous reaction performed over a ZnCl2 catalyst in the conventional solvent dichloromethane, higher regioselectivity of the 'para' cycloadduct and excellent yield were achieved at shorter reaction time in these ionic liquids with optimized molar compositions of MX and ZnCl2. These moisture-insensitive ionic liquids can be easily separated from reaction products after simple washing with hexane, allowing their reuse with no obvious loss in activity.
- Yin, Donghong,Li, Changzhi,Li, Biaomo,Tao, Liang,Yin, Dulin
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p. 137 - 142
(2007/10/03)
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- Cycloaddition Of Carbonyl Compounds To Olefins At Aluminosilicate Catalysts
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The use of zeolite catalysts in the reactions of allocimene and myrcene with α,β-unsaturated carbonyl compounds makes the reaction conditions milder and increases both the regio- and the stereoselectivity of the diene synthesis processes.In the reaction of certain polyenes with aldehydes at ascanite-bentonite clay a new reaction, leading to bicyclic ethers, was discovered.
- Volcho, K. P.,Tatarova, L. E.,Korchagina, D. V.,Salakhutdinov, N. F.,Aul'chenko, I. S.,et al.
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p. 683 - 694
(2007/10/02)
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- EFFICIENT CYCLOADDITION DURING ADSORPTION ON CHROMATOGRAPHIC SOLVENTS
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An essentially new method was developed for carrying out cycloaddition on the surface of chromatographic adsorbents in the absence of solvent.This method permits the use of much milder reaction conditions and to increase the reaction's selectivity.
- Veselovskii, V. V.,Gybin, A. S.,Lozanova, A. V.,Moiseenkov, A. M.,Smit, V. A.
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- DRAMATIC ACCELERATION OF THE DIELS-ALDER REACTION BY ADSORPTION ON CHROMATOGRAPHY ADSORBENTS
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The development of a new method for effecting cycloadditions on the surface of chromatographic adsorbents in the absence of solvents that leads to a moderation of the reaction conditions and an increase in selectivity is described.
- Veselovsky, V. V.,Gybin, A. S.,Lozanova, A. V.,Moiseenkov, A. M.,Smit, W. A.,Caple, R.
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p. 175 - 178
(2007/10/02)
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