[shrapnash]

I recently read that preparation of phenylamine can be done through reduction of nitrobenzene by refluxing with Sn and conc. HCl followed by NaOH. It is mentioned that LiAlH4 cannot be used for the reduction as some side reactions will occur. Any idea as to what the "side-reactions" are ?

[sjb]

Well, there's always the raft of intermediates in nitro group reduction, though I'd've thought LAH would also reduce them as well

ArNO₂ -> ArNHOH -> ArNO -> ArNH₂

or via the azo species

ArN=NAr, ArN=N(O)Ar etc.?

Does anyone have a copy of M. Hudlicky, Reductions in Organic Chemistry., The Royal Society of Chemistry, Cambridge, U.K., 1996., or similar to hand?