3-Nitro-2-naphthalenemethanol: a photocleavable protecting group for carboxylic acids |
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Authors: | Anil K Singh Prashant K Khade |
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Institution: | Department of Chemistry, Indian Institute of Technology, Bombay, Powai, Mumbai 400 076, India |
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Abstract: | 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. |
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Keywords: | 3-Nitro-2-naphthalenemethanol Photocleavable protecting group Caging |
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