Abstract
Azo Bridges from Azines, XII., – Transannular Hydroboration of Close Parallel CC and NN BondsIn the systems 3 and 5 9‐borabicyclo[3.3.1]nonane (9‐BBN) adds to the close parallel CC/NN bonds in a transannular reaction. A B – N bond is formed and the borane hydrogen transferred to the CC bond regio‐ and stereospecifically. The structure of the adducts 4 and 6 is elucidated by NMR spectroscopy and in the case of 4a by an X‐ray analysis. The catecholborane 9 forms with 3 an azo – borane adduct at first, pointing to a stepwise transannular reaction.
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