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 оригинала | английский |
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Страницы (с-по) | 7238-7243 |
Число страниц | 6 |
Журнал | Journal of Organic Chemistry |
Том | 84 |
Номер выпуска | 11 |
DOI | |
Состояние | Опубликовано - 7 июн. 2019 |