Journal of the Chemical Society. Perkin transactions I p. 2841 - 2848 (1982)
Update date:2022-08-05
Topics:
Fukata, Gouki
Sakamoto, Naoya
Tashiro, Massashi
Preparation of 4-azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone (3) from 4-bromo-2,4,6-tri-t-butylcyclohexa-2,5-dienone (1) and sodium azide is described.Treatment of (3) with concentrated sulphuric acid afforded 2,6-di-t-butyl-p-benzoquinone (7) in 75percent yield, while the reaction at -10 deg C in chloroform solution gave a tri-t-butylazepinone (5) and 3,5-di-t-butyl-o-benzoquinone (8).Photolysis of (3) in benzene afforded 2,4-di-t-butylcyclopenta-2,4-dienone (11), which was isolated as the dimer (12).Thermolysis of (3) in boiling toluene gave 6-amino-2,4-di-t-butylphenol (17), 2,4,6,8-tetra-t-butyl-1H-phenoxazin-1-one (21), and 2-cyano-9,9a-dihydro-3,5,7,9a-tetra-t-butylcyclopenta<1,4>benzoxazin-1(3aH)-one (22) in 15, 15 and 48percent yields, respectively.When the thermolysis was carried out with very low reagent concentrations, 5-cyano-2,4-di-t-butylcyclopenta-2,4-dienone (23), in addition to the phenol (17), was obtained.The compound (23) was also obtained by thermolysis of (3) in boiling acetic anhydride and in boiling toluene containing acetic anhydride.The reaction pathway for the formation of compounds (17), (22), and (23) on thermolysis of the azide (3) is also discussed.
View MoreHANGZHOU YUNUO CHEMICAL CO.,LTD
website:http://www.yunuochem.com
Contact:0571-83715115
Address:hangzhou
NINGBO PANGS CHEM INT’L CO.,LTD.
Contact:+86-574-27666845
Address:FLOOR 21,BUILDING NO.11,XIN TIAN DI,NO.689 SHI JI ROAD,NINGBO CHINA
VanderArk International Limited
Contact:86-10-82437576
Address:Qing He
Xi'an Kaixiang Photoelectric Technology Co., Ltd
website:http://www.kxmaterials.com/
Contact:86-29-15991651477
Address:Building 6, Biopharmaceutical Industry R&D Cluster Base, No. 16, Caotang 4th Road, Caotang Science and Technology Industrial Base, High-tech Zone, Xi'an City, Shaanxi Province, China
Jiangsu Institute of Ecomones Co., Ltd
website:http://www.jsmone.com
Contact:+86-519-82821700
Address:95 Huanyuan N. Road, Jintan, Jiangsu, China
Doi:10.1016/0040-4020(80)80102-5
(1980)Doi:10.1016/j.tetlet.2014.03.105
(2014)Doi:10.1023/B:COHC.0000018339.22815.13
(2003)Doi:10.1021/ja047052z
(2004)Doi:10.1002/jhet.5570170601
(1980)Doi:10.1016/j.bmcl.2004.07.080
(2004)
