Synlett 2007(7): 1172-1173  
DOI: 10.1055/s-2007-977431
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Oxalyl Chloride: A Versatile Reagent in Organic Synthesis

David Rodrigues da Rocha*
Instituto de Química, Universidade Federal Fluminense, CEP: 24020-150, Niterói, Rio de Janeiro, Brazil
e-Mail: davidrrocha@uol.com.br;
Further Information

Publication History

Publication Date:
13 April 2007 (online)

Introduction

Oxalyl chloride is a very versatile reagent extensively used by organic chemists. One of its most common uses is in oxidation of alcohols to aldehydes and ketones named Swern oxidation. [1-5] However, this reagent can efficiently be applied in many other reactions such as 1,1-cycloadditions with 1,4-dilithio-1,3-dienes or zirconacyclopentadienes, [6] cyclization of 1,3-bis(trimethylsilyloxy) alk-1-enes to isoeletronic acids, [7] preparation of phenyl isocyanates from anilines, [8] bicyclization of biaryl acetamides, [9] dehydration of formamides to afford nitriles, [10] and ­cyclization of 1,1-bis(trimethylsilyloxy) ketene acetals to give 3-hydroxymaleic anhydrides. [11]

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