Journal of the Chemical Society. Perkin transactions I p. 1277 - 1286 (1996)
Update date:2022-08-03
Topics:
Ishii, Akihiko
Maeda, Kiyoto
Kodachi, Maki
Aoyagi, Noriko
Kato, Keiko
Maruta, Teruo
Hoshino, Masamatsu
Nakayama, Juzo
Synthesis of 8-hydroxy-4-methylthiophenetriptycene 1 was performed by treatment of the trilithium salt, prepared from 1,1,1-tris(2-bromo-4-methyl-3-thienyl)ethane 13, with diethyl carbonate. In a similar manner, the 8-hydroxy-4-ethylthiophenetriptycene 27 was prepared. The isomeric 4-hydroxy-8-methyl derivative 11 was also obtained by reaction of the trilithium salt, derived from 1,1,1-tris(3-bromo-5-methyl-2-thienyl)ethane 40, with dimethyl carbonate. Attempts to prepare 8-hydroxy-4-tert-butyl- 31 and 8-hydroxy-4-unsubstituted thiophenetriptycenes resulted in the formation of ketone 29 and hydroperoxide 32, respectively. The 8-hydroxy-4-methylthiophenetriptycene 1 decomposed to the corresponding ketone 26 on heating. Attempts to generate the carbocation at the bridgehead of compound 1 by dissolution in conc. H2SO4 or by acetolysis of methanesulfonate 44 were unsuccessful. 8-Acetoxy (45) and 8-methoxy (46) derivatives of compound 1 were prepared by treatment of compound 1 with acetic anhydride in triethylamine in the presence of DMAP and by methylation of the lithium salt of compound 1 with trimethyloxonium tetrafluoroborate, respectively. Comparison of IR spectra of regioisomers 1 and 11 indicated that hydrogen bonding of the bridgehead hydroxy group in compound 1 is somewhat hampered by the steric hindrance of the sulfur atoms of the three thiophene rings.
View Morewebsite:http://www.NEM.COM.CN
Contact:+86-393-4411771
Address:The west section of shengli Road,Puyang,Henan Province,China
Kunshan Yalong Trading Co,.Ltd
Contact:86-512-57621185
Address:805-807 Room Hongqiao Mansion ,1088 West Qianjin Road, Kunshan, Jiangsu，China
Hebei Lead Bio-Chemicals Co., Ltd.
website:http://www.ldbiochem.com
Contact:+86-311-87826503
Address:481, Heping West Road, Shijiazhuang,China
ShanDong XinDa Chemical CO.,LTD(expird)
Contact:086-0311-87580543
Address:No.168, High Technology Development Zone Jinan Shandong China
Chengdu Baishixing Science and Technology Industry Co., Ltd.
website:http://www.cd-bsx.com
Contact:+86-28-88531548
Address:#217,North of Industry Road,Heshan Town,Pujiang County,Chengdu,Sichuan,China.
Doi:10.1039/d0dt03414b
(2020)Doi:10.1016/0040-4039(96)00874-X
(1996)Doi:10.1039/b201304e
(2002)Doi:10.1039/jr9570000137
(1957)Doi:10.1016/j.tetlet.2012.07.115
(2012)Doi:10.1016/0040-4039(96)01013-1
(1996)
