Journal of the Chemical Society. Perkin transactions I p. 107 - 113 (1996)
Update date:2022-09-26
Topics:
Armesto, Diego
Gallego, Mar G.
Horspool, William M.
Ramos, Ana
While the aza-di-π-methane rearrangement is the normal photoreactive behaviour of β,γ-unsaturated imines and oxime acetates, the results obtained in this study show that 1,3-migrations of acetoxyimino groups in β,γ-unsaturated oxime acetates takes place only when all the parameters are correct. The rearrangement takes place when there is a quaternary carbon separating the two π-systems and when one of the radical centres in the intermediate cyclobutyl 1,4-biradical is stabilized by conjugation with a phenyl ring. Suppression of the free rotor effect also helps to promote the reaction. These criteria are fulfilled in compounds 1a and 7a. The reaction was extended to the β,γ-unsaturated oximes 1b and 7b where again the 1,3-migration of the oximino group took place. Copyright 1996 by the Royal Society of Chemistry.
View MoreNingbo Inno Pharmchem Co., Ltd.
Contact:86-574-87319282
Address:6F-5,NO.163 RUIQING RD.,NINGBO 315000 CHINA
Shanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Hangzhou yi lu biont technology Co., LTD
Contact:+86-571-88152630
Address:Hangzhoushi HuafengRoad Yicheng3Building1001room.
Yancheng Creator Chemical Co., Ltd
Contact:0086-515-88710008 88710068 88710858 88710868
Address:No.21 Renming Road, Longgang Town, Yandu County,Yancheng City
Liaoyang hengye Chemical Co., Ltd.
Contact:86-419-5850866
Address:North Old Xiaoxiao Road,Yantai District, Dengta, Liaoyang, Liaoning, China
Doi:10.1016/j.bmc.2014.02.054
(2014)Doi:10.1021/jo960289w
(1996)Doi:10.1007/BF00945376
()Doi:10.1039/CC9960000789
(1996)Doi:10.1021/jo951948s
(1996)Doi:10.1021/jacs.9b08342
(2019)