Journal of Organic Chemistry p. 7309 - 7316 (2017)
Update date:2022-08-04
Topics:
Ding, Xiong
Wang, Pengfei
The excited state meta effect, also known as the meta-ortho effect, results from selective electron transmission from an electron-donating group to the meta and ortho sites on an aromatic ring in its first excited singlet state. This effect facilitates photochemical cleavage of benzylic C-O or C-N bond to release the corresponding alcohol, carboxylic acid, or amine when an electron-donating amino group is at the meta position, as demonstrated in our recent work of using a 3-diethylaminobenzyl (DEABn) group as an effective photolabile protecting group (PPG). Herein, we demonstrate that an ortho amino group can also facilitate benzylic C-O bond cleavage to release an alcohol or carboxylic acid. However, an amino group at the meta position results in a PPG with better overall chemical and photochemical properties.
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Doi:10.1021/jf001127a
(2001)Doi:10.1021/acs.orglett.7b01632
(2017)Doi:10.1021/jo00910a008
(1975)Doi:10.1246/cl.1975.779
(1975)Doi:10.1021/jo00911a025
(1975)Doi:10.1021/ja01612a048
(1955)