Allyl phenylacetate

The reaction mechanism (Scheme 6.25) involves formation of a cationic 7t-allylpalladium complex by the oxidative addition of the substrate onto the catalyst. In case of a dimethylallyloxycarbonyl protecting group this step is disfavoured compared to Alloc and therefore the removal of dimethylallyl groups is slower or requires more catalyst. Accordingly, in homogeneous CH3CN/H2O solutions deprotection of (allyl)phenylacetate proceeded instantaneously with 2 mol % [Pd(OAc)2]/TPPTS while it took 85 min to remove the dimethylallyl group (cinnamyl is an intermediate case with 20 min required for complete deprotection). The reactivity differences are... 

SYNS ALLYL PHENYLACETATE BENZENE-ACETIC ACID, 2-PROPENYL ESTER PHENYLACETIC ACID ALLYL ESTER... 

Allyl a-toluate. See Allyl phenylacetate Allyl 2,4,6-tribromophenyl ether. See Tribromophenyl allyl ether Allyl trichloride. See 1,2,3-Trichloropropane Allyltrimethoxysilane CAS 2551-83-9 EINECS/ELINCS 219-855-8 Synonyms Silane, allyltrimethoxy- Silane, trimethoxy-2-propenyl Trimethoxy-2-... 

Benzeneacetic acid, 2-phenylethyl ester. See Phenethyl phenylacetate Benzeneacetic acid 2-propenyl ester. See Allyl phenylacetate... 

Acetylfuran Allyl disulfide Allyl isovalerate Allyl octanoate Allyl phenylacetate... 

Allyl phenylacetate Allyl propionate Allyl propyl disulfide Allyl sorbate Allyl sulfide Allyl tiglate Allyl 10-undecenoate Ambrettolide Ammonium isovalerate Ammonium sulfide... 

Allyl caproate Allyl cinnamate Allyl cyclohexaneacetate Allyl cyclohexanebutyrate Allyl cyclohexanehexanoate Allyl cyclohexanepropionate Allyl cyclohexanevalerate Allyl disulfide Allyl 2-ethy I butyrate Allyl heptanoate Allyl a-ionone Allyl isothiocyanate Allyl isovalerate Allyl mercaptan Allyl nonanoate Allyl octanoate Allyl phenoxyacetate Allyl phenylacetate Allyl propionate Allyl sorbate Allyl sulfide Allyl tiglate Allyl 10-undecenoate Ambrettolide Ammonium isovalerate Ammonium sulfide Amyl acetate n-Amyl alcohol Amyl butyrate o-Amylcinnamaldehyde a-Amylcinnamaldehyde dimethyl acetal a-Amylcinnamyl acetate o-Amylcinnamyl alcohol a-Amylcinnamyl formate a-Amylcinnamyl isovalerate Amyl formate Amyl 2-furoate Amyl heptanoate Amyl hexanoate Amyl octanoate Amyl salicylate p-Anisaldehyde Anisole p-Anisyl acetate p-Anisyl alcohol Anisyl butyrate Anisyl formate Anisyl phenylacetate Anisyl propionate Benzaidehyde... 

Allyl phenylacetate Benzyl methacrylate Cinnamaldehyde ethylene glycol acetal Cinnamyl acetate Ethyl cinnamate... 

Moreover D-configuration could also be determined for the auxins (-l-)- -allyl-phenylacetic acid, (—)-indane carboxylic acid and (-)-i,2,3,4-tetrahydro-i-naphthoic acid (LVIII, LIX, LX). 

Dibenzyl ether reacted with Mg after five days of reflux in THF to give phenylacetic acid in 42% yield after carbonation. Maercker(99) was able to obtain a 15% yield of 3-butenoic acid from allyl methyl ether after 56 h of reflux. 

Honey Allyl phenoxyacetate, phenylaceiate Benzyl cinnamate Carvacryl acetate Cinnamyl butyrate p-Cresyl acetate p-Cresyl ethyl ether /rt-Cresyl phenylaceiate />-Cresyl phenylaceiate Cyclohexyl phenylacctate Ethyl phenoxyacetate. phenylaceiate Guaiol phenylaceiate Isobutyl phenylaceiate Linalyl butyrate Methyl phenylaceiate Phenethyl acetate, butyrate, phenylaceiate Phenylacetic acid Propyl phenylaceiate Santalyl phenylaceiate. 

The allyl group in the allylphenols can be oxidized, after protecting the hydroxyl group, to yield substituted phenylacetaldehydes 78 - 76 76 and phenylacetic acids. Thus, homogentisic acid LXIII is prepared readily by ozonizing the dibenzoate of allylhydroqumone LXIV, which is obtained by rearrangement of the allyl ether of hydroquinone mono-... 

Benzyl halides have been reported to react with nickel carbonyl to give both coupling and carbonylation (59). Carbonylation is the principal reaction in polar nonaromatic solvents, giving ethyl phenylacetate in ethanol, and bibenzyl ketone in DMF. The reaction course is probably similar to that of allylic halides. Pentafluorophenyl iodide gives a mixture of coupled product and decafluorobenzophenone. A radical mechanism has been proposed (60). Aromatic iodides are readily carbonylated by nickel carbonyl to give esters in alcoholic solvents or diketones in ethereal solvent (57). Mixtures of carbon monoxide and acetylene react less readily with iodobenzene, and it is only at 320° C and 30 atm pressure that a high yield of benzoyl propionate can be obtained (61). Under the reaction conditions used, the... 

For the N-terminal deprotection of peptides, the enzyme penicillin G acylase from E. coli has been applied. This attacks phenylacetic acid (PhAc) amides and esters but does not hydrolyze peptide bonds [12-14,25]. The danger of a competitive cleavage of the peptide backbone at an undesired site, which always exists when proteases like trypsin and chymotrypsin are used, is overcome by using the acylase. The penicillin G acylase accepts a broad range of protected dipeptides (27) as substrates, and selectively liberates the N-terminal amino group under almost neutral conditions (pH 7-8, room temperature), leaving the peptide bonds as well as the C-terminal methyl-, allyl-, benzyl-, and tert-butyl ester unaffected (Fig. 8) [25a,bj. On the other hand, the phenylacetamide... 

For the preparation of long chain alkanes from fatty acids it is useful to extract the electrolyte contin-ously with a high-boiling nonpolar solvent, e.g. 2-methylheptane. Cyclopropanecarboxylic acids in some cases have been dimerized, e.g. or (15) in other cases the radical is further oxidized to a carbocation which then undergoes ring opening and solvoiysis to allylic compounds. Specifically substituted 1,2-diphenyiethanes have been prepared from phenylacetic acids (Table 2, entries 22 and 23). A variety of 2,3-disubstituted succinic acids and their derivatives have become accessible from malonic... 

In the deprotection of phenylacetic allyl esters over Pd(OAc)2/TPPTS catalysts, it was noted that the reaction medium plays a role in determining reaction selectivity. The reaction is shown below in Eq. (1). When the reaction is performed homogeneously in CH3CN/H20 as the solvent, the allyl substituents with Rt = R2 = H Rj = Ph, R2 = H Rj = R2 = Me are all substituted [20, 21] the first in the series is the fastest to react. In contrast, when the reaction takes place under biphasic conditions in C3H7CN/H20, only the simple allyl ester, R, — R2 — H, is cleaved. When two allylic esters are incorporated into a single molecule the allyl ester can be selectively substituted under two-phase reaction conditions. 

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