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3-Nitro-2-naphthalenemethanol: a photocleavable protecting group for carboxylic acids

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Title 3-Nitro-2-naphthalenemethanol: a photocleavable protecting group for carboxylic acids
 
Creator SINGH, ANIL K
KHADE, PRASHANT K
 
Subject chromophore
carboxylic acid
photochemistry
 
Description Photocleavable protecting groups are important in synthesis and caging. Among many such groups, 2-nitrobenzyl and related groups have been found useful in many applications. However, most of the known 2-nitrobenzyl-based caging chromophores show either low quantum yield or the photolysis wavelength is not suitable for various applications. In this paper, we report 2-nitro-3-naphthalenemethanol (NNM) as an efficient photocleavable protecting group for molecules containing a carboxylic function. NNM possesses photochemical properties better than the 2-nitrobenzyl chromophores as it is photoactivatable at 380 nm in aqueous medium (CH3CN/H2O, 3:2 v/v) showing the desired photochemistry. The carboxylic acids are efficiently photoreleased from NNM-based esters in almost quantitative yield.
 
Publisher Elsevier
 
Date 2009-02-19T11:26:46Z
2011-11-25T17:33:00Z
2011-12-26T13:06:27Z
2011-12-27T05:54:17Z
2009-02-19T11:26:46Z
2011-11-25T17:33:00Z
2011-12-26T13:06:27Z
2011-12-27T05:54:17Z
2005
 
Type Article
 
Identifier Tetrahedron 61(42), 10007-10012
0040-4020
http://dx.doi.org/10.1016/j.tet.2005.08.019
http://hdl.handle.net/10054/712
http://dspace.library.iitb.ac.in/xmlui/handle/10054/712
 
Language en