Redox chemistry of a hydroxyphenyl-substituted borane.
Chemical reduction of a hydroxyphenyl-substituted borane triggers a sequential electron- and intramolecular hydrogen-atom-transfer process to afford a hydridoborate phenoxide dianion. On the other hand, hydrogen-atom abstraction of the borane leads to the isolation of a neutral borylated phenoxyl radical, which can be transformed to the corresponding benzoquinone borataalkene derivative by reduction with cobaltocene.
Department of Chemistry, National Taiwan University, No.1, Sec. 4, Roosevelt Rd., Taipei, 10617 (Taiwan).
Po-Yeng
PY
Feng
Yi-Hung
YH
Liu
Tien-Sung
TS
Lin
Shie-Ming
SM
Peng
Ching-Wen
CW
Chiu
boranes; electron transfer; free radicals; hydrogen-atom transfer; reduction