Tetrahedron p. 2577 - 2592 (1987)
Update date:2022-07-29
Topics:
Glover, Stephen A.
Goosen, Andre
McCleland, Cedric W.
Schoonraad, Johan L.
N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1
View MoreContact:86-21-34622192，13917187091，21-34622765
Address:No. 500 Caobao Road Shanghai P.R China
Contact:86-512-87182055
Address:No.128 Fangzhou Rd, Suzhou Industrial Park, China, 215125, China
Hebei Lead Bio-Chemicals Co., Ltd.
website:http://www.ldbiochem.com
Contact:+86-311-87826503
Address:481, Heping West Road, Shijiazhuang,China
Contact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Wuxi Zuping Food Science And Technology Co.,LTD.
Contact:+86-510-87210822
Address:Guanlin town
Doi:10.1039/b713129a
(2008)Doi:10.1002/anie.200800929
(2008)Doi:10.1016/j.saa.2007.10.045
(2008)Doi:10.1002/ejoc.202000117
(2020)Doi:10.1016/j.tetlet.2008.05.152
(2008)Doi:10.1016/S0040-4020(01)81921-9
(1993)
