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Synlett 2012(1): 157-158  
DOI: 10.1055/s-0031-1290104
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Rongalite

Jiu-Xi Chen*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
e-Mail: jiuxichen@wzu.edu.cn;
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Publikationsverlauf

Publikationsdatum:
13. Dezember 2011 (online)

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Introduction

Rongalite (also known as sodium formaldehyde sulfoxylate or sodium hydroxymethanesulfinate) is a versatile, inexpensive and readily available reagent, which has been employed twenty years ago. [¹] It is commonly used in the textile industry as a decolorizing agent. Several reports are available in the literature demonstrating its utility in organic synthesis. For example, rongalite is capable of producing the perfluoroalkyl free radicals via dehalogenation of alkyl halides, [²-4] such as direct perfluoroalkylation of pyridines, [5] coumarins [6] and 2-quinolones. [7] It has been also used for the cleavage of diaryl disuldes and diselenides generating the corresponding chalcogenolate species in situ that then undergo facile ring opening and acylation, affording β-hydroxy sulfides, [8] thioesters and selenoesters, [9] respectively. It was also found to be a sulf­oxylate dianion equivalent in the conversion of dihalides into sultine derivatives. [¹0-¹5]

Rongalite is commercially available, but it can also be readily prepared by reaction of formaldehyde with sodium sulfite. [¹6]

Scheme 1

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