How, chemically, would you remove protruding phenyl groups? I mean for instance in the molecule phenethylamine there's a phenyl group sticking out (or protruding) how would you go about removing this phenyl group?

2-phenylethan-1-amine to ethanamine

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    $\begingroup$ The only method I'm aware of for removing arbitrary alkyl substituents from benzene is reversed Friedel-Craft (treating the substance with a Lewis acid catalyst under acidic conditions at very high temperature). With a primary carbon attached, extremely harsh conditions are required, and the possibility of side reactions will likely yield a mixture of polysubstituted benzenes and, if you're lucky, some of your substituent in a recoverable form. At those extreme conditions, however, I frankly have no idea if your amine group will actually survive without autoigniting or otherwise degrading. $\endgroup$ – Greg E. Mar 26 '13 at 13:02
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    $\begingroup$ @GregE. I think that your example would serve as a fine answer if you wanted to convert your comments into a full response. $\endgroup$ – jonsca Apr 2 '13 at 4:03
  • $\begingroup$ You might try doing artificial evolution in the lab with ribozymes, thus achieving high selectivity and high rates after only a couple of cycles. It's pretty equipment-heavy and not really suited for Chem.SE, though. Also it is pretty non-trivial to find a suitable starting molecule. $\endgroup$ – tschoppi May 3 '15 at 13:14
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    $\begingroup$ FWIW, Reaxys has a grand total of zero hits for this specific transformation. $\endgroup$ – orthocresol Oct 12 '16 at 10:51

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