SIDE-CHAIN HYDROXYLATION OF AROMATIC-COMPOUNDS BY FUNGI .4. INFLUENCE OF THE PARA-SUBSTITUENT ON KINETIC ISOTOPE EFFECTS DURING BENZYLIC HYDROXYLATION BY MORTIERELLA-ISABELLINA
被引:21
作者:
HOLLAND, HL
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机构:Department of Chemistry, Brock University, St. Catharines
HOLLAND, HL
BROWN, FM
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机构:Department of Chemistry, Brock University, St. Catharines
BROWN, FM
CONN, M
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机构:Department of Chemistry, Brock University, St. Catharines
CONN, M
机构:
[1] Department of Chemistry, Brock University, St. Catharines
来源:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
|
1990年
/
10期
关键词:
D O I:
10.1039/p29900001651
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The benzylic hydroxylation of a series of para-substituted toluenes by the fungus Mortierella isabellina has been studied by using CD3, CHD 2, and CH2D methyl labelled substrates. Inter- and intramolecular primary and secondary deuterium kinetic isotope effect ratios have been determined: the intermolecular primary effects are maximal with strongly electron-withdrawing para substituents (R = CN and CF3), while the intramolecular primary effects are minimal for R = H but increase in instances where R is electron donating or withdrawing. These results are interpreted in terms of a dependence of the hydroxylation mechanism on the nature of the para substituent.