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 MoreNanyang Tianhua pharmaceutical Co.,Ltd.
Contact:+8618639816203
Address:Longsheng Industrial Park
Shanxi Tongji Pharmaceuticals Co., Ltd.
Contact:+86-359-3024784
Address:Xikuang South Road, Ruicheng County , Shanxi
QINGDAO HONG JIN CHEMICAL CO.,LTD.
website:http://www.hongjinchem.com
Contact:+86-532-83657313
Address:2ND Building, 8 Shangqing Road, Qingdao, Shandong Province, China.
Shanghai Yuking Water Soluble Material Tech Co., Ltd
Contact:86-21-68286299
Address:4F, 13B, No. 600, South Xinyuan Road 201306, Shanghai, China
Jinan Yijialian Economic and Trade Development Co., Ltd.
Contact:+86 0531-66729596
Address:jinan
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)
