Journal of Organic Chemistry p. 4986 - 4992 (1988)
Update date:2022-08-04
Topics:
Adam, Waldemar
Kliem, Ulrike
Mosandl, Thomas
Peters, Eva-Maria
Peters, Karl
Schnering, Hans Georg von
The visible-laser photochemistry of 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one (1) with benzoquinone (BQ) and with phenanthraquinone (PQ) in an argon atmosphere afforded the expected regioisomeric oxetane products 2 and 3.Under an oxygen atmosphere, trapping of the Paterno-Bouchi preoxetane intermediates by molecular oxygen was observed for BQ, leading to the regioisomeric and stereoisomeric 1,2,4-trioxanes 4-BQ and 5-BQ.Regioselectivity, favoring the acetal-type structures 2 and 4, appears to follow diradical stability.Anomeric effects are invoked to rationalize the stereochemical course of the trioxane trapping products.The lactone-acetal structure 4 represents the first qinghaosu-type (artemisin) 1,2,4-trioxane.
View MoreJinan Boss Chemical Industry Co., Ltd.【revoke the business license】
website:http://www.chemboss.com.cn
Contact:+86-531-58591595
Address:No2.Hualong Road, Jinan, China
Lanzhou huibang biological chemical technology Co., LTD
Contact:0931-7843964
Address:NO.2011,Yannan Road,Chengguan,
Suzhou HeChuang Chemical Co.,Ltd.
Contact:+86-512-88800520
Address:No.9 Guanchao Rd,Changshu Advanced Materials Industy Park
website:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
Jiangxi Hessence Chemicals Co., Ltd.
Contact:+86 796 3511924
Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
Doi:10.1021/acs.orglett.9b03556
(2019)Doi:10.1055/s-1988-27550
(1988)Doi:10.1021/jo00262a032
(1989)Doi:10.1055/s-0028-1088038
(2009)Doi:10.1016/S0008-6215(00)82581-1
(1982)Doi:10.1055/s-0028-1088019
(2009)