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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 4
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Original Articles

Efficient Reduction of Aryl Azides and Aryl Nitro Compounds to Their Corresponding Amines with Sulfurated Calcium Borohydride CA(BH2S3)2. A New Modified Borohydride Agent

H. Firouzabadi Chemistry Department, College of Science, Shiraz University, Shiraz, 71454, Iran
,
B. Tamami Chemistry Department, College of Science, Shiraz University, Shiraz, 71454, Iran
&
A. R. Kiasat Chemistry Department, College of Science, Shiraz University, Shiraz, 71454, Iran
Pages 587-596 | Received 22 Mar 1999, Accepted 18 Jun 1999, Published online: 04 Dec 2007
 
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Abstract

Ca(BH2S3)2 is easily prepared by metathetical reaction between NaBH2S3 and CaCl2 in THF. Ca(BH2S3)2 is much more stable than NaBH2S3 therefore, is a more practical reagent. Sulfurated calcium borohydride can easily reduce aryl nitro and aryl azido functions to their amines in high yields in refluxing THF. Reduction of nitro groups is accompanied with regioselectivity. Very high chemoselectivity is also observed for the reduction of an azido functional group in the presence of nitro functionality.

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Related Research Data

Synthesis and Crystal Structure of 1,3-Bis(p-nitrophenoxy)propane
Source: Springer Science and Business Media LLC
Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse
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Organic Azides: An Exploding Diversity of a Unique Class of Compounds
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