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Synlett 2009(7): 1185-1186  
DOI: 10.1055/s-0028-1088112
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Malonyl Dichloride

Leandro José dos Santos*
Departamento de Química, Universidade Federal de Minas Gerais, UFMG, Belo Horizonte, CEP 31.270-901 Minas Gerais, Brazil
e-Mail: ljquimica@yahoo.com.br;
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Publication History

Publication Date:
02 April 2009 (online)

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Introduction

Malonyl dichloride, or malonyl chloride CH2(COCl)2, is widely used in organic synthesis as a versatile biselectrophilic reagent. This compound has been used mainly in acylation (O-, S-, N-, C-acylation) and alkylation reactions. It is a convenient reagent for the preparation of heterocyclic derivatives [¹-8] and is utilized as an important building block in the synthesis of supramolecular compounds [9-¹²] with several applications. An attractive use of malonyl dichloride is the formation of the bicyclo[3.3.1]nonane-trione system [¹³-¹5] in a one-pot reaction. Compounds containing this bicyclo system are common features incorporated into the structures of numerous natural products. Malonyl dichloride must be handled with precaution because it is lachrymating and corrosive. Due to the reaction with water it decomposes when exposed to wet air.