American Chemical Society
Browse
om8b00598_si_002.xyz (50.78 kB)

Accessing Two-Stage Regioselective Photoisomerization in Unsymmetrical N,C-Chelate Organoboron Compounds: Reactivity of B(ppz)(Mes)Ar

Download (50.78 kB)
dataset
posted on 2018-09-20, 19:13 authored by Cally Li, Soren K. Mellerup, Xiang Wang, Suning Wang
A new family of unsymmetrical, N,C-chelate organoboron compounds B­(ppz)­(Mes)­Ar have been synthesized and found to undergo a rare, regioselective two-stage photoisomerization, involving the Ar group only. The initial transformation is a Zimmerman rearrangement to afford yellow azaboratabisnorcaradiene isomers that are subsequently converted to unprecedented 14aH-diazaborepins via a photochemical “walk” rearrangement. Spectroscopic and computational studies provide insight into the formation and properties of these unique systems.

History