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Synlett 2002(6): 1017-1018
DOI: 10.1055/s-2002-31924
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Thallium Trinitrate (TTN)

Tiago Oliveira Vieira*
Instituto de Química, Universidade de São Paulo, C. P. 26077, CEP 05508-900, São Paulo, Brazil
e-Mail: tiagovieira@hotmail.com;
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Publication History

Publication Date:
07 February 2007 (online)

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Introduction

Thallium(III) salts have proved to be very versatile reagents to oxidize a great variety of organic functionalities, as attested by the several review articles in the field. [1] [2] They are highly toxic and must be handled with care. However, they are not cumulative, since they are excreted in urine. The three most common salts are the thallium triacetate (TTA), thallium tris-trifluoroacetate (TTFA) and thallium trinitrate (TTN), the latter having the broader application.

TTN was firstly employed in organic synthesis, during the 70’s, in the oxidation of olefins and ketones, leading, respectively, to aldehydes and carboxylic acid derivatives, as reviewed by McKillop. [3] TTN is highly ionic and shows great solubility either in inorganic or in organic solvents. TTN can also be supported on clays, such as Montmorillonite K-10. The thallium(I) nitrate formed in the end of the reactions is insoluble in almost all common solvents. Thus, the reaction can often be monitored by the formation of a precipitate, which can be easily separated from the product by filtration.

Another important aspect is the poor nucleophilicity of the nitrate ion. In this way, it is rarely incorporated into the final product.