Journal of Organic Chemistry p. 1077 - 1083 (1991)
Update date:2022-07-30
Topics:
Padwa, Albert
Zhi, Lin
Fryxell, Glen E.
A series of 8-oxabicyclo<3.2.1>oct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of α-diazopentanedione with various alkynes.The photochemical behavior of these oxabicyclic enones was investigated.Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift.A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered.The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined.The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis.The photochemistry of the homologous 7-oxabicyclo<2.2.1>hepten-2-one was studied.The results obtained can be interpreted in terms of an initial Norrish type I cleavage.The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.
View MoreContact:+86-371-86058576
Address:NO.32, Jingsan Road, Zhengzhou, China
Hangzhou Yanshan Chemical Co.,Ltd.
Contact:86-571- 87698076
Address:Room 1001, #1 Building, Zhongtian MCC, No.2 Youzhinong, Wenyi West Road, Xihu District, Hangzhou, China
Kunshan Yalong Trading Co,.Ltd
Contact:86-512-57621185
Address:805-807 Room Hongqiao Mansion ,1088 West Qianjin Road, Kunshan, Jiangsu,China
website:http://www.acrospharmatech.com
Contact:+1-3234804688
Address:Flat/RM 1502,Easey Commercial building 253-261 Hennessy Road,Wanchai,HongKong
website:http://www.afinechem.com
Contact:+86-571-85134551
Address:No. 206 Zhen Hua Road, Hangzhou 310030, Zhejiang, China
Doi:10.1021/ic201593s
(2011)Doi:10.1016/j.bmcl.2011.08.102
(2011)Doi:10.1016/j.ejmech.2011.08.022
(2011)Doi:10.1021/ja00012a066
(1991)Doi:10.1039/P19920001637
(1992)Doi:10.1021/acs.orglett.8b02703
(2018)