1-Phenylethyl benzoate

Similar studies were conducted with 1-phenylethyl benzoate derivatives labeled with, sO (radioactive) or, 70 (NMR active) carbonyl groups. Substituents in the alkyl groups and in the leaving group affect both the rates and the nature of the carbenium ion intermediates. For example, 1-phenylethyl p-nitrobenzoate undergoes solvolysis [Eq. (19)] at 60° C in 70% aqueous acetone 30,000 times slower than the corresponding l-(p-methoxyphenyl)ethyl derivative [54]. 

Powell believed that the reaction proceeds through the in situ generation of benzoate 57 which then undergoes a coupling reaction with 46. The key evidence supporting this hypothesis was the observation of this intermediate in the initial stages of the reaction (via 1H NMR). Furthermore, 1-phenylethyl benzoate 57... 

DEAMINATION OF AMINES. 2-PHENYLETHYL BENZOATE VIA THE NITROSOAMIDE DECOMPOSITION... 

C. 2-Phenylethyl benzoate. The carbon tetrachloride solution of N-nitroso-N-(2-phenylethyl)benzamide (Note 4) and 0.1 g. of sodium carbonate (Note 5) are placed in a 200-mi. round-bottomed flask equipped with a condenser, and the mixture is heated under reflux for 24 hours. The evolution of nitrogen ceases, and the yellow color of the nitrosoamide disappears near the end of this period. The solution is washed with 5% sodium hydroxide solution, water, and dried. The solvent is removed under reduced pressure and the 2-phenylethyl benzoate distilled b.p. 138-142° (1 mm.), yield 5.8-6.1 g. [56-59% based on N-(2-phenylethyl) benzamide]. 

N-Nitroso-N-(2-phenylethyl)benzam-ide, from nitrosation of N-(2-phenylethyl)benzamide, 47, 45 thermolysis to 2-phenylethyl benzoate, 47, 45... 

Oxidation of amides (White deamination) [follows 1, 327], White223 has described the benzoylatien of 2-phenylethylamine (1), the reaction of (2) with dinitrogen tetroxide to give (3), which on thermal decomposition at 77° affords 2-phenylethyl benzoate (4). 

Benzoic acid, 2-phenylethyl ester 2-phenylethyl benzoate 3547, 4249 ... 

Benzyl carbinyl benzoate Phenethyl alcohol, benzoate Phenylethyl benzoate 2-Phenylethyl benzoate... 

Phenylethyl benzoate 2-Phenylethyl benzoate P-Phenylethyl benzoate. See Phenethyl... 

Benzyl benzoate Benzyl-m-cinnamate Benzyl /ra .s-cinnamate p-Phenylethyl benzoate P-Phenylethyl cinnamate p-Phenylethyl dihydrocinnamate... 

Figure 2.5. Nucleophile selectivities determined from product analysis for the reactions of ring-suhstituted 1-phenylethyl derivatives (X-l-Y) with azide ion, acetate ion and methanol in 50 50 (v/v) water/trifluoroethanol. The selectivities are plotted against the appropriate Hammett substituent constant or a. Leaving group Y ( ) ring-suhstituted benzoates ( ) chloride (T) dimethyl sulfide (A) tosylate.

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