The First Spirobifluorenes Containing Two Binaphthyl Moieties

Alexander G. Russell; Neil S. Spencer; Douglas Philp; Benson M. Kariuki; John S. Snaith

doi:10.1021/om030422s

The First Spirobifluorenes Containing Two Binaphthyl Moieties

Alexander G. Russell, Neil S. Spencer, Douglas Philp, Benson M. Kariuki, John S. Snaith^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The first spirobifluorenes which comprised of two binaphthyl moieties with silicon and germanium at the site of fusion were synthesized and fully characterized. The compounds were prepared by lithiation of 2,2′-dibromobinaphthyl (78 to -30°C) and subsequent treatment of the dilithio species with 0.5 equiv of silicon tetrachloride or germanium tetrachloride, followed by chromatography over silica gel. X-ray crystallography analysis revealed that both molecules possessed highly distorted structures, which resulted in a low barrier for interconversion between the two atropisomers. The barrier was calculated from the temperature dependency of the nuclear magnetic resonance spectra.

Original language	English (US)
Pages (from-to)	5589-5592
Number of pages	4
Journal	Organometallics
Volume	22
Issue number	26
DOIs	https://doi.org/10.1021/om030422s
State	Published - Dec 22 2003

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The first spirobifluorenes which comprised of two binaphthyl moieties with silicon and germanium at the site of fusion were synthesized and fully characterized. The compounds were prepared by lithiation of 2,2′-dibromobinaphthyl (78 to -30°C) and subsequent treatment of the dilithio species with 0.5 equiv of silicon tetrachloride or germanium tetrachloride, followed by chromatography over silica gel. X-ray crystallography analysis revealed that both molecules possessed highly distorted structures, which resulted in a low barrier for interconversion between the two atropisomers. The barrier was calculated from the temperature dependency of the nuclear magnetic resonance spectra.",

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AU - Russell, Alexander G.

AU - Spencer, Neil S.

AU - Philp, Douglas

AU - Kariuki, Benson M.

AU - Snaith, John S.

PY - 2003/12/22

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AB - The first spirobifluorenes which comprised of two binaphthyl moieties with silicon and germanium at the site of fusion were synthesized and fully characterized. The compounds were prepared by lithiation of 2,2′-dibromobinaphthyl (78 to -30°C) and subsequent treatment of the dilithio species with 0.5 equiv of silicon tetrachloride or germanium tetrachloride, followed by chromatography over silica gel. X-ray crystallography analysis revealed that both molecules possessed highly distorted structures, which resulted in a low barrier for interconversion between the two atropisomers. The barrier was calculated from the temperature dependency of the nuclear magnetic resonance spectra.

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The First Spirobifluorenes Containing Two Binaphthyl Moieties

Abstract

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