Benzylic halides (entries 1 and 5–9) as well as benzyl acetates, carbonates, phosphates, or tosylates (entries 2–4 and 6) can be coupled.

Potential electron donors can be C or Sb. Reaction characteristics of Diels–Alder reactions in high-temperature liquid water and supercritical water are attributed to the unique properties of near-critical and supercritical water [27,119,120]. The bulk of benzyl acetate is used in soap odors, but it is also popular for other perfumes and is used to a minor extent in flavors (1980).

A temperature of 600°C was found to be optimal.

More interestingly, the authors described the use of chiral ligands in combination with racemic secondary benzyl acetates, obtaining promising yields and stereoinductions with (S,S)-BDPP or (R,R)-i-Pr-DUPHOS. The latter was proposed to rapidly react with CO to afford an acyl cobalt intermediate that promotes a hydrosilylation. In addition, the elevated pressure increases the reaction rate since Diels–Alder reactions have a high activation volume of about − 25 to − 50 cm3/mol [116]. In 2016, Chen and Han disclosed complementary protocols for the reaction between benzyl pivalates and phenyl acetonitrile derivatives giving either benzylation products or the corresponding stilbene derivatives resulting from HCN elimination (Scheme 57).105 In both reports, a broad range of benzyl substrates and nucleophiles was presented, encompassing both π-extended backbones and phenyl-type substrates. That is a problem for nonpolar components in an aqueous environment at room temperature. Scheme 35. [citation needed], InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3, InChI=1/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3, Except where otherwise noted, data are given for materials in their,, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Articles with unsourced statements from September 2008, Creative Commons Attribution-ShareAlike License, This page was last edited on 12 October 2020, at 00:43. Peter J. Harrington, in Comprehensive Organometallic Chemistry II, 1995, Allyl ethers, allyl carboxylates, allyl carbonates, and allyl carbamates can all be readily cleaved using tributyltin hydride, a palladium phosphine catalyst, and a proton source such as acetic acid or p-nitrophenol. (256).

Column chromatography of the residue on silica gel, eluting with 63:37 hexane–acetone, gave the title compound as a pale yellow liquid (3.92 g, 78% yield relative to benzyl acetate).

The excess dimethyl methylphosphonate and unreacted benzyl acetate were removed by distillation under vacuum (35 °C at 0.2 mmHg). In condensation reactions, two or more molecules combine to a larger molecule and release a simple molecule like H2O, HCl, or NH3, as, for example, in the formation of esters. Unfortunately, however, significant amounts of styrenes were observed, probably due to competitive β-hydride elimination with secondary benzyl acetates. Found in essential oils of bergamot, lavender, lavandin, spike lavender, Clary sage, neroli and petitgrain. It seemed that the incorporated Sb favors the formation of the undesired carbon deposits. The reaction of n-butyraldehyde to 2-ethyl-3-hexanal occurs with complete conversion and 85% selectivity at T = 275 °C [2]. La dernière modification de cette page a été faite le 6 décembre 2019 à 12:08. The customary mechanism of ester hydrolysis, via addition of hydroxide to the carbonyl carbon (69), should not show such a rate disparity.

The interested reader is referred to the reviews on organic reactions in high-temperature liquid and supercritical water [2,22,23,25,27]. Reprinted with permission from Gatla, S., Mathon, O., Rogalev, A., et al. As expected, PdO and PdCl2 after treatment with air atmosphere and metallic Pd after treatment with He atmosphere were detected as main phases. DPEPhos=(Oxydi-2,1-phenylene)bis(diphenylphosphine). But, the atmosphere did not influence the time of the activation period. The description of those reactions is considered to be outside the scope of this book.

Such behavior can be explained through transfer of electron density to Pd from another component of the catalytic system. The tin hydride reductive cleavage is chemoselective: allylic carboxylates can be reduced even in the presence of aldehydes, Families of compounds that occur in essential oils, Essential Chemistry for Aromatherapy (Second Edition), Bee Venom Composition: From Chemistry to Biological Activity, Aida A. Abd El-Wahed, ... Hesham R. El-Seedi, in, Comprehensive Organic Synthesis II (Second Edition), Organoborane reagents are employed most frequently (entries 1–5), but methods for the coupling of organosilane (entry 6), organotin (entry 7), organozinc (entry 8), or organoindium reagents (entry 9) have also been developed.

Drugs for Treating Respiratory System Diseases, ). We use cookies to help provide and enhance our service and tailor content and ads.

The aldehyde that is liberated undergoes an additional hydrosilylation to deliver the silyl ether product. Benzyl acetate is an organic ester with the molecular formula C9H10O2. Summarizing this complex system, XPS displayed clearly that the coexistence of both Pd and PdO was necessary for active catalysts.


Tunge and Chruma have reported decarboxylative processes via C(sp3)–O cleavage for the installation of alkynes and ketones at the benzylic position (Scheme 56).103 Unfortunately, the scope of these reactions is essentially limited to substrates with π-extended backbones. The allyl and alloxycarbonyl strategy is orthogonal to the benzyloxycarbonyl (BOC) and the t-butoxycarbonyl strategies (t-BOC).17–18, When a proton source is omitted from the recipe, reductive cleavage results in isolable tin-containing products. The Diels–Alder reaction is the most widely used synthetic method for the production of polycyclic ring compounds. Contamination by tin residues is apparently not a problem. Scheme 34. The Journal of Physical Chemistry C 121, 3854-3861. J. Radnik, in Encyclopedia of Interfacial Chemistry, 2018.

Ni-catalyzed reactions of phenyl acetonitrile derivatives with benzyl pivalates. Hydrothermal and Supercritical Water Processes, Supercritical Fluid Science and Technology, .

G. Manolikakes, in Comprehensive Organic Synthesis II (Second Edition), 2014. Prompted by Murai's report, Legros and Fiaud studied the possibility of promoting Pd-catalyzed C–C bond-forming reactions of benzyl acetates with dimethylmalonates (Scheme 54).98 The authors found that the reaction remained limited to benzylic acetates derived from substrates with extended π-backbones, an observation that was attributed to the requirement for partial dearomatization via π-allyl-Pd complexes. δP (121.5 MHz, CDCl3) 32.5 ppm. Alloxycarbonyl is easily introduced using inexpensive and commercially available allyl chloroformate. X-ray diffraction investigation revealed that during the activation, PdO was reduced to metallic Pd, whereas the metallic Pd remained stable.

Similar to most other esters, it possesses a sweet and pleasant aroma, owing to which, it finds applications in personal hygiene and health care products. Unfortunately, after reaching maximum activity the system deactivates, which mean activity declines. On le trouve à l'état naturel dans beaucoup de fleurs. Complex polypeptide synthesis often requires the use of several protection–deprotection strategies. Such investigations are very sensitive for changes of Pd 4d valence band. Here, after the activation both states, oxidic and metallic, were detected for Pd independently of the pretreatment.

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