Dendrimeric catalysts for the activation of hydrogen peroxide. Increasing activity per catalytic phenylseleno group in successive generations

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1043-1046

  Francavilla, Charles ^a   Bright, Frank V ^a   Detty, Michael R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000110384     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990836a     Document Type: Article

References (28)

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25. 13C NMR spectra were consistent with ≥97% purity. Spectral and analytical data for the new compounds of this study can be found in the Supporting Information.
26. -3 M diphenyl ether internal standard. The organic phase was sampled periodically by gas chromatography, and initial rates are reported on the basis of the first 25% of reaction.
27. 2 was added (approximately 1 h). After 3 h, the cyclohexene was consumed and 4.05 g ( 16.7 mmol) of 25 and 4.51 g (25.2 mmol) of 26 were isolated, which corresponds to 41.9 mmol (84% yield) of brominated product from 0.008 mmol of 24 (a turnover number of > 5200). Under identical conditions, catalyst 17 (0.010 mmol) gave 10.3 mmol of brominated products after 3 h for a turnover number of > 1030. In the latter reaction, starting cyclohexene had not yet been consumed. The catalysts were recovered from the organic phase following a bisulfite wash and chromatography on silica. No loss of catalytic activity was observed upon further use.
28. Naidoo, K. J.; Huches, S. J.; Moss, J. R. Macromoloecules 1999. 32, 331-341.