Titanium dioxide photocatalysis of adamantane

被引：50

作者：

Cermenati, L ^{[1
]}

Dondi, D ^{[1
]}

Fagnoni, M ^{[1
]}

Albini, A ^{[1
]}

机构：

[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 34期

关键词：

oxidation; alkanes; photocatalysis; titanium dioxide; alkylation; RADICAL CATIONS; ALKANES; FUNCTIONALIZATION; OXIDATION; CHAIN; PHOTOOXIDATION; ACETONITRILE; DEGRADATION; HYDROCARBON; ACTIVATION;

D O I：

10.1016/S0040-4020(03)01092-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

TiO2 photocatalysis of adamantane in oxygen equilibrated MeCN yields 1- and 2-adamantanol and adamantanone with limited degradation and preference for functionalization at the 1 position, particularly in the presence of silver salts. Oxidation in CH2Cl2 is less selective. The oxidation of cyclohexane and cyclododecane is slower. In N-2-flushed solutions with Ag+ as a sacrificial acceptor, products from the trapping of both 1-adamantyl radical (adamantyl methyl ketone) and cation (N-adamantylacetamide) are obtained. Furthermore, alkylation of an electrophilic alkene (isopropylydenmalononitrile) has been obtained, though in a low yield. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6409 / 6414

页数：6

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