Hindered rotation about single bonds baa been observed in a wide variety of molecules. Recent investigations of substituted butadienes have used nmr techniques to characterize this phenomenon, which renders these molecnles cbirall. We wish to report the preparation of hydrocarbons~and~, substituted
Sterically hindered internal rotation in acyclic hydrocarbons: Tetraisopropylethylene
β Scribed by David S. Bomse; Thomas Hellman Morton
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 216 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
In continuation of our studies of sterically crowded, acyclic hydrocarbons with hindered rotation about carbon-carbon single bondsI, we have prepared tetraisopropylethylene, BL, and its tetradeuterio 2 analogue, lb, by the reductive coupling reaction of McMurry and Fleming, reaction 1. Compound&, which is sublimed out of the reaction mixture at 130Β°C under a steady stream of nitrogen, is obtained from 2,4-dimethyl-3-pentanone in 12qbyield: colorless needles, mp 125-125.5'C, ir (KBr pellet) 3050,
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The rotational barriers in bis(2,4,Ctri-tert-butylphenyl) diselenide and ditelluride have been investigated by total line-shape analysis of variabletemperature 'H NMR spectra in CFCI,-CD,CI, (85: 15). The free energies of activation, AGf,,, K, for the diselenide and ditelluride were determined to be