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#1 2008-10-29 12:48:27


iodotriphenylmethane reduction w sodium bisulfite to triphenylmethane

I don't know if a direct answer to the title question is on the internet or not, however, let me answer this question with mechanistic thinking.

From wikipedia, you can learn sodium bisulfite chemistry,

Sulfite can act as a nucleophile in addition to aldehydes, for example:

Sulfite is also used to reduce halogen to halides, for example:

It seems logical then that a direct addition to iodine could give the triphenylmethane anion. Protonation will give triphenylmethane.

If this reaction seems abnormal to you, you should consider what I have written about atomic structure in "A Guide to Organic Chemistry Mechanisms" (, Barnes and Noble or ). An alternate model to the Pauling electronegativity arguments is presented in which a consistent argument for the halogens, the second row elements (C, N, O, and F) is made. That rational would predict that iodine would be a better reaction for this reduction than Br, Cl, or F.


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