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Azobrücken aus Azinen, XII. Transannulare Hydroborierung von parallel benachbarten CC/NN‐Bindungen
Author(s) -
Brand Uwe,
Hünig Siegfried,
Peters Karl,
Schnering Hans Georg Von
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240534
Subject(s) - chemistry , borane , adduct , hydroboration , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , hydrogen bond , double bond , molecule , polymer chemistry , organic chemistry , catalysis
Azo Bridges from Azines, XII., – Transannular Hydroboration of Close Parallel CC and NN Bonds In 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.