Journal of the Chemical Society. Perkin transactions I p. 2069 - 2076 (1996)
Update date:2022-08-04
Topics:
Banks, R. Eric
Besheesh, Mohamed K.
Mohialdin-Khaffaf, Suad N.
Sharif, Iqbal
Methods of synthesis are described for a range of 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts [R-N+(CH2CH2)3N+-F (X-)2, where R = CH3, CH2Cl, C2H5, CF3CH2, C8H17 and (X-)2 = (TfO-)2, (BF4-)2, (PF6-)2, (TfO-, BF4-), (TfO-, PF6-), (TfO-, FSO3-)] by direct fluorination (with neat F2 at ≤20 mmHg or F2-N2 blends at 1 atm pressure) of monoquaternary salts of 1,4-diazabicyclo[2.2.2]octane [R-+N(CH2CH2)3N X-] or their 1:1 adducts with boron trifluoride, phosphorus pentafluoride, or sulfur trioxide in acetonitrile at ca - 35°C. The results of site-selective electrophilic fluorination of diethyl sodio(phenyl)malonate [→ PhCF(CO2Et)2], 1-morpholinocyclohexene (→ 2-fluorocyclohexanone), phenol (→ 2- and 4-FC6H4OH), 1- and 2-hydroxynaphthalene (→ 2- and 4-FC10H6OH, and 1-FC10H6OH and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene, respectively), acetanilide (→ 2- and 4-FC6H4NHCOCH3), anisole (→ 2- and 4-FC6H4OCH3) and sodium benzenesulfinate (→ PhSO2F) with these N-fluoroammonium salts are presented.
View MoreTaizhou volsen chemical Co., Ltd
website:http://www.volsenchem.com
Contact:+86-576-88869393
Address:Jiaojiang District, Taizhou, Zhejiang, China.
Shanghai Hanshare Industry Co.,Ltd.
Contact:86 21 20960688
Address:RM902-903,Building E, Wanda Plaza,No.26,Zhoukang Road, Pudong District, Shanghai, China
Jewim Pharmaceutical (Shandong) Co., Ltd
Contact:+8615621883869
Address:山东省泰安市高新技术产业开发区配天门大街西首
Hangzhou Showland Technology Co., Ltd.
Contact:86-571-88920516
Address:ROOM2118,NO.553,WENSAN ROAD,HANGZHOU,CHINA
MTT Pharma & Bio-technology Co.,Ltd(expird)
Contact:+86-21-58407925
Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, China
Doi:org/10.1016/j.tetlet.2012.09.003
(2012)Doi:10.1039/c2cc36044f
(2012)Doi:10.1039/c39920000348
(1992)Doi:10.1021/acs.orglett.9b01230
(2019)Doi:10.1021/jo00929a045
(1974)Doi:10.1021/ja00036a077
(1992)
