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Volumn 10, Issue 8, 2008, Pages 1513-1516

Cooperative brønsted acid-type organocatalysis: alcoholysis of sytrene oxides

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Indexed keywords


EID: 49349100124     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800149y     Document Type: Article
Times cited : (97)

References (25)
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    • Suprisingly. reaction times in all cases are nearly equal, although GC/MS analysis after 15 h showed more than two times faster conversion in case of 7 mol, of 3 than in case of our standard protocol 1 mol, of 3, The results are available in the Supporting Information
    • Suprisingly. reaction times in all cases are nearly equal, although GC/MS analysis after 15 h showed more than two times faster conversion in case of 7 mol % of 3 than in case of our standard protocol (1 mol % of 3). The results are available in the Supporting Information.
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    • We observed a nonlinear catalytic effect for the ethanolysis of 1 with a notable rate enhancement in the second half of the reaction period. This is apparently not a case of autocatalysis through product 4b because addition of 20 mol% of 4b to our standard test reaction showed no variation relative to our standard protocol. Further mechanistic investigations are currently underway.
    • We observed a nonlinear catalytic effect for the ethanolysis of 1 with a notable rate enhancement in the second half of the reaction period. This is apparently not a case of autocatalysis through product 4b because addition of 20 mol% of 4b to our standard test reaction showed no variation relative to our standard protocol. Further mechanistic investigations are currently underway.
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    • Frisch; et al. Gaussian 03 (for full reference see Supporting Information).
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