Journal of Organic Chemistry p. 10 - 18 (1985)
Update date:2022-08-05
Topics:
Fristad, William E.
Peterson, John R.
The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.
View MoreTIANJIN FESTO CHEMICAL CO.,LTD
Contact:86-22-25814570
Address:No.12th,5th Ave.,TEDA,Tianjin,China
Contact:+86-571-86491666
Address:SHI XIANG ROAD
Henan Yellow River New Material Technology Co.Ltd.
website:http://www.yellowriverchem.com
Contact:0086-373-7278760
Address:Chengguan Town, Yuanyang County
Xiamen Huasing Chemicals Co.Ltd.
Contact:0086-592-6228397
Address:NO.24, Xinglin North 2nd Road,Jimei district
Luojiang Chenming Biological Products Co
Contact:+86 15000297032
Address:GROUP NO.4, HE SHENG VILLAGE, PANLONG TOWN,
Doi:10.1016/j.bmcl.2009.10.059
(2009)Doi:10.1246/bcsj.49.3239
(1976)Doi:10.1021/ja00447a039
(1977)Doi:10.1021/om0304311
(2003)Doi:10.1039/DT9770000120
()Doi:10.1016/j.bmc.2006.02.012
(2006)