Journal of Organic Chemistry p. 10736 - 10742 (2018)
Update date:2022-08-11
Topics:
Ding, Xiong
Wang, Pengfei
Herein we demonstrate that the photolabile protecting group (PPG), the 1-[3-(diethylamino)-phenyl]ethyl (DEAPE) group, has dramatically different photochemical properties from the parent 3-(diethylamino)benzyl (DEABn) PPG. The new PPG, derived from DEABn by adding a methyl group to the benzylic carbon, has similar reactivity as DEABn in releasing alcohol in MeCN/water; however, it is more efficient than DEABn in releasing carboxylic acid. In particular, it can release carboxylic acid efficiently in aprotic solvents and the PPG itself converts to 3-diethylaminostyrene. Photochemical removal of DEAPE can also be conveniently carried out with sunlight. The results in this work suggest that there probably exist multiple reaction pathways in cleaving the benzylic C-O bond and they can be affected by the benzylic substitution and the reaction conditions.
View MoreContact:+86-10-59484199
Address:No.58-A1026 Liangguan Street
NIGNXIA XINDACHANG TECHNOLOGY CO.,LTD
website:https://xdcchemical.com/
Contact:86-311-85758226
Address:North Industry Area, Wuji
Contact:+86-27-67841589
Address:Add: 999 Gaoxin Road, Donghu New Technology Development Zone, Wuhan City, Hubei, China
SHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Contact:0086 371 65711996
Address:Jalan 4/3, Kawasan Perindustrian Serendah, 48000 Rawang,
Doi:10.1071/CH12181
(2013)Doi:10.1021/j100211a042
(1982)Doi:10.1021/op200066e
(2011)Doi:10.1039/jr9320000298
(1932)Doi:10.1002/cctc.201601290
(2017)Doi:10.1002/adsc.201401086
(2015)