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31.28.1.7.2 Variation 2: Using Primary or Secondary Amines

DOI: 10.1055/sos-SD-031-01728

Scholz, U.; Schlummer, B.Science of Synthesis, (2007311591.

Older procedures describe the replacement of bromine atoms with p-toluidine using strongly basic conditions, such as in the synthesis of N,N-di-4-tolylbenzene-1,3-diamine (65) from 1,4-dibromobenzene and p-toluidine (Scheme 70).[‌146‌] The shift in the substitution pattern of the central arene in the product 65 is an indication that this reaction proceeds via an aryne mechanism.

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References


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