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Synlett 2003(14): 2263-2264  
DOI: 10.1055/s-2003-42110
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Sulfur Trioxide-Amine Adducts

B. Sc. Damien Kelly*
Department of Chemistry, National University of Ireland, Galway, Ireland.
Fax: +353(91)525700; e-Mail: damien.kelly@nuigalway.ie;
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Publication History

Publication Date:
29 October 2003 (online)

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Introduction

Many developments have taken place throughout the history of sulfonating reagents from the synthesis of stabilized liquid SO3 1 to the production of chlorosulfonic acid (ClSO3H) and the development of SO3-amine adducts. Reactions involving SO3 and ClSO3H prove to be quite violent and are accompanied with heat liberation. With such violent reactivity characteristics a milder reagent was sought. It has been long known that chlorosulfonic acid added dropwise and at low temperatures reacts with aliphatic and aromatic tertiary amines to produce the corresponding sulfur trioxide amine complexes (O3S -__N+R3) for example, O3S -__N+(CH3)3, 1 O3S -__N+(CH2CH3)3 and O3S -__N+(CH2CH2CH3)3. [1] Sulfur trioxide amine adducts are valuable and versatile sulfonating agents. They may be utilised in the sulfation of alcohols (formation of S-O bonds), sulfonation of acid sensitive heterocycles, aliphatic and aromatic hydrocarbons (formation of S-C bonds) and the sulfamation of amines (formation of S-N bonds). [2] The resulting products have quite diverse properties, for example, they may act as dyes, detergents, sweeteners, pharmaceutical intermediates, herbicides etc.

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