Journal of Organic Chemistry p. 4491 - 4495 (1992)
Update date:2022-09-26
Topics:
Adam, Waldemar
Heil, Markus
Hutterer, Rudi
The 3-halo-substituted 1,2-dioxetane 1 was employed as mechanistic probe in the reaction with NADH model compounds, namely, three N-substituted 1,4-dihydronicotinamides and 9,10-dihydro-10-methylacridine (AcrH2), to differentiate between the direct hydride ion transfer and the electron transfer (SET) mechanisms.While AcrH2 led mostly to cleavage into carbonyl products, the nicotinamide reduced the dioxetane 1 to yield the epoxy alcohol 3 as the main product.Additionally, the diol 2, the cleavage product bromoacetone, and the dehalogenation product acetone were observed.The formation of 3 is interpreted in terms of direct hydride ion transfer from the nicotinamides to the dioxetane with subsequent bromide elimination of the intermediary alkoxide.The dehalogenation product acetone was taken as evidence for initial electron transfer.
View Moreshanghai tuomiao chemicial co.,ltd.
website:https://www.tuomiaochem.com/
Contact:021 - 59853336
Address:shanghai
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Hubei Onward Bio-Development Co., Ltd.
Contact:+86-718-8417012
Address:No.517,Shizhou Avenue,Enshi City,Hubei Province,China,445002
LinHai Cina Chemical Co., LTD.
Contact:0576-85580989
Address:Pharma-chem zone,Duqiao,Linhai,Zhejiang,China
He Bei Shun Er Chemical Co., LTD.
Contact:86-0311-86996932/86860168
Address:No 18,North street
Doi:10.1021/cm400333c
(2013)Doi:10.1016/j.ejmech.2012.11.036
(2013)Doi:10.1002/chem.201600341
(2016)Doi:10.1016/j.bmc.2017.12.039
(2018)Doi:10.1016/j.poly.2013.01.038
(2013)Doi:10.1016/j.bmc.2012.12.054
(2013)