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 MoreJinan Yijialian Economic and Trade Development Co., Ltd.
Contact:+86 0531-66729596
Address:jinan
website:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
YanCheng LongShen Chemical Co.,Ltd.
Contact:+86-515-86668866
Address:No.13,Weiyi Road,Funing Aoyang Industrial Park
Baoding City Light Industry And Textiles Imp.& Exp. Corp. Chemical Department.
Contact:86-312-3262436
Address:NO.658 CHAOYANG SOUTH STREET,BAODING CITY HEBEI CHINA
Shijiazhuang Frontierchem Co., Ltd.
Contact:+86-311-89271196
Address:4-4-202 No.15 Biandian Street,Shijiazhuang
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)
