研究者情報 | 神奈川大学

チカライシ　ノリコ Chikaraishi Noriko 力石　紀子所属神奈川大学理学部理学科職種助教
言語種別	英語
発行・発表の年月	2016/01
形態種別	学術雑誌
査読	査読あり
標題	Influences of alpha-substitutent in 4,5-dimethoxy-2-nitrobenzyl-protected esters on both photocleavage rate and subsequent photoreaction of the generated 2-nitrophenyl ketones: A novel photorearrangement of 2-nitrophenyl ketones
執筆形態	共著
掲載誌名	Journal of photochemistry and photobiology A: Chemistry
掲載区分	国外
出版社・発行元	Elsevier Ltd
巻・号・頁	321,pp.41-47
担当範囲	Experiments, preparation of the manuscript
著者・共著者	◎Noriko Chikaraishi Kasuga, Yusuke Saito, Nomichi Okamura, Tatsuya Miyazaki, Hikaru Satou, Kazuhiro Watanabe, Takaaki Ohta, Shu-hei Morimoto, Kazuo Yamaguchi
概要	Ultraviolet (UV)-induced photodeprotection of 2-nitrobenzyl esters to release the acid with formation of the corresponding 2-nitrosoketone proceeds rapidly when the alpha-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 alpha-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.