3 Цитирования (Scopus)

Аннотация

Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.

Язык оригиналаанглийский
Страницы (с-по)7238-7243
Число страниц6
ЖурналJournal of Organic Chemistry
Том84
Номер выпуска11
DOI
СостояниеОпубликовано - 7 июн 2019

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