Phenethyl

Acetoxylation and nitration. It has already been mentioned that 0- and m-xylene are acetoxylated as well as nitrated by solutions of acetyl nitrate in acetic anhydride. This occurs with some other homologues of benzene, and with methyl phenethyl ether,ii but not with anisole, mesitylene or naphthalene. Results are given in table 5.4. 

Ph.CH2.OMe, Ph.(CH2)2.0Me, Ph.(CH2)3.0Me (2-3, 3-4, 1-3), does not decrease steadily, but goes through a maximum. These two circumstances point to a specific -interaction in nitrations of the ethers with acetyl nitrate which is important with benzyl methyl ether, more important with methyl phenethyl ether, and not important with methyl phenpropyl ether. This interaction is the reaction with dinitrogen pentoxide already mentioned, and the variation in its importance is thought to be due to the different sizes of the rings formed in the transition states from the different ethers. 

PEA from pENZYL ALCOHOL AND BETA-PHENETHYL ALCOHOL] (Vol 4)... 

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