Determination of the absolute structure of the chiral crystal consisting of achiral dibutylhydroxytoluene and asymmetric autocatalysis triggered by this chiral crystal

[Display omitted] Absolute structure is determined of chiral crystal composed of achiral dibutylhydroxytoluene (BHT, 2,6-di-tert-butyl-p-cresol) by single crystal X-ray diffraction and circular dichroism. Left-handed (M-) crystals exhibited a positive Cotton effect at a wavelength of approximately 2...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2016-10, Vol.27 (19), p.943-946
Main Authors: Matsumoto, Arimasa, Takeda, Sora, Harada, Shunya, Soai, Kenso
Format: Article
Language:English
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Summary:[Display omitted] Absolute structure is determined of chiral crystal composed of achiral dibutylhydroxytoluene (BHT, 2,6-di-tert-butyl-p-cresol) by single crystal X-ray diffraction and circular dichroism. Left-handed (M-) crystals exhibited a positive Cotton effect at a wavelength of approximately 288nm observed using KBr disk [CD(+)288KBr]. In contrast, right-handed (P-) crystals exhibited a negative Cotton effect at the same wavelength [CD(−)288KBr]. Asymmetric autocatalysis is triggered by the chiral crystals of achiral BHT, i.e., M-(+)-BHT afforded (S)-pyrimidyl alkanol and P-(−)-BHT afforded (R)-pyrimidyl alkanol.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2016.07.013