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- W2289788112 abstract "Ultraviolet(UV)-induced photodeprotection of 2-nitrobenzyl esters to release the acid with formation of the corresponding 2-nitrosoketone proceeds rapidly when the α-position in the 2-nitrobenzyl group is substituted by a branched alkyl group. The generated 2-nitrosophenyl ketones undergo multiple photoreactions, including a unique photorearrangement, depending upon the nature of the α-substituent. 2-Nitrosoketone bearing an isopropyl substituent mainly undergoes this rearrangement to afford a bicyclic oxazole via a shift of the isopropyl group to the bridgehead position, resulting in loss of aromaticity of the six-membered ring. 2-Nitrosopheyl ketone bearing a tertiary-butyl substituent gives mainly azoxy and azo compounds via intermolecular reaction of nitrosoketones with loss of isobutene. The photorearrangement does not proceed in the case of the phenyl-substituted compound. These findings will be helpful for the selection and/or design of photolabile protecting groups." @default.
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- W2289788112 date "2016-05-01" @default.
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- W2289788112 title "Influences of alpha-substituent in 4,5-dimethoxy-2-nitrobenzyl-protected esters on both photocleavage rate and subsequent photoreaction of the generated 2-nitrosophenyl ketones: A novel photorearrangement of 2-nitrosophenyl ketones" @default.
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- W2289788112 doi "https://doi.org/10.1016/j.jphotochem.2016.01.012" @default.
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