Selective catalytic oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide:: a coproduct-free route to phenol

被引：69
作者：
Arends, IWCE
Sasidharan, M
Kühnle, A
Duda, M
Jost, C
Sheldon, RA
机构：
[1] Delft Univ Technol, Dept Biotechnol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
[2] CREAVIS Gesellschaft Technol & Innovat mbH, D-45764 Marl, Germany
来源：
TETRAHEDRON | 2002年 / 58卷 / 44期
关键词：
autoxidation; cyclobexylbenzene; phenol; N-hydroxyphthalimide;
D O I：
10.1016/S0040-4020(02)01131-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method is described for the highly selective oxidation of cyclohexylbenzene to cyclohexylbenzene-1-hydroperoxide. In the presence of 0.5 mol% N-hydroxyphthalimide (NHPI) and 2 mol% of the hydroperoxide product, without solvent, a selectivity of ca. 98% to the desired product was obtained at 32% conversion. The use of NHPI increases the selectivity for initial H-abstraction from the 1-position, vs the other positions in the cyclohexyl ring, suppresses byproduct formation via transannular hydrogen abstraction and increases the overall rate of reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
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页码：9055 / 9061
页数：7
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