In class, we learned about the Clemmensen reduction of carbonyl groups to the corresponding hydrocarbon. This is all well and good, except that it would also seem that the conditions used in the Clemmensen reduction might also affect other groups, such as the reduction of nitro groups to amino groups.

Generally, would a Clemmensen reduction have any affect on either an aromatic or aliphatic amino group within the compound? If so, I am assuming that a protecting group would then be necessary. I know that nitro groups will be reduced to amino groups, and am also wondering if they would then be further acted upon by the reaction conditions.

  • 2
    $\begingroup$ What could happen to the amino groups? $\endgroup$ – DHMO Jan 25 '17 at 16:37
  • $\begingroup$ I am not exactly sure right now. $\endgroup$ – Jeffrey Jan 25 '17 at 16:41
  • $\begingroup$ I don't have time to write an actual answer right now, but amines are usually tolerated. Secondary and tertiary without issue, primary have some potential issues. $\endgroup$ – NotEvans. Jan 26 '17 at 1:22

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