Chemical Communications 2012-05-14

Rearrangement from the heteroantiaromatic borole to the heteroaromatic azaborine motif.

Sunanda Biswas, Cäcilia Maichle-Mössmer, Holger F Bettinger

Index: Chem. Commun. (Camb.) 48(38) , 4564-6, (2012)

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Abstract

Treatment of 9-chloro-9-borafluorene with N,O-bis(trimethylsilyl)hydroxylamine results in 10-trimethylsilyloxy-9-aza-10-boraphenanthrene 6b. NMR spectroscopy shows that the expected antiaromatic 9-(trimethylsilyloxyamino)-9-borafluorene 5b rearranges to the formally aromatic phenanthrene 6b at room temperature.This journal is © The Royal Society of Chemistry 2012