Abstract

Reaction of the strongly electrophilic borane trans-pentenyl-B(C6F5)2 (5) with TEMPO gave the 2:1 addition product (C6F5)2B(ONHR2)CHCHCH(ONR2)-C2H5 (8), (NR2 = tetramethylpiperidinyl). It is thought to be formed by TEMPO addition to the boron atom followed by H-atom abstraction at the allylic CH2 group followed by the addition of a second equivalent of TEMPO. The dihydroboroles (11a,b) react with one molar equivalent of TEMPO to form dimeric bis-borane TEMPO addition products (14a,b).

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