53129-28-5Relevant articles and documents
Synthesis of podands bearing aromatic end groups and complex formation with tropylium tetrafluoroborate in 1,2-dichloroethane
Laemsae, Markku,Raitamaa, Kirsi,Pursiainen, Jouni
, p. 557 - 563 (2007/10/03)
A series of podands bearing phenyl, naphthyl and anthryl end groups were prepared and characterized. UV-visible spectrophotometry was used to investigate the host-guest chemistry of the podands in complexation with tropylium tetrafluoroborate in 1,2-dichloroethane. The results, are discussed and compared with those for previously studied systems containing crown ethers. The stability constants for these open-chain polyethers are in the range 5,1-8,4 dm3 mol-1, except for the podand having anthryl end groups [1,12 bis(anthryl-9)-2,5,8,11-tetraoxadodecane], which gives a 10-fold increase in the stability constant. Copyright
The Development of a New Nitrating Agent: The Unusual Regioselective Nitration of Diphenylpolyethylene Glycols and Phenylpolyethylene Glycols with Trimethylsilyl Nitrate - BF3OEt2
Kimura, Masaru,Kajita, Kazushige,Onoda, Naoyuki,Morosawa, Shiro
, p. 4887 - 4892 (2007/10/02)
We have investigated the nitration of the following podands, 1-phenoxy-8-(2'-nitrophenoxy)-, 1-phenoxy-8-(4'-nitrophenoxy)-, and 1-(2',4'-dinitrophenoxy)-8-phenoxy-3,6-dioxaoctane (2, 3, and 4), and 1-(2',4'-dinitrophenoxy)-11-phenoxy-3,6,9-trioxaundecane (5), 1-phenoxy-3,6,9-trioxadecane (6), and 1-phenoxy-3,6,9,12-tetraoxatridecane (7), with trimethylsilyl nitrate catalyzed by BF3OEt2, which is soluble in nonpolar solvents.The reaction selectivity was measured by the ortho:para ratio of the nitrated products and was unusually large in CCl4.The structures of all isolated products, 1,8-bis(2'-nitrophenoxy)-, 1-(2'-nitrophenoxy)-8-(4'-nitrophenoxy)-, 1,8-bis(4'-nitrophenoxy)-, 1-(2',4'-dinitrophenoxy)-8-(2'-nitrophenoxy)-, and 1-(2',4'-dinitrophenoxy)-8-(4'-nitrophenoxy)-3,6-dioxaoctane (8, 9, 10, 11, and 12), 1-(2',4'-dinitrophenoxy)-11-(2'-nitrophenoxy)- and 1-(2',4'-dinitrophenoxy)-11-(4'-nitrophenoxy)-3,6,9-trioxaundecane (13 and 14), 1-(2'-nitrophenoxy)- and 1-(4'-nitrophenoxy)-3,6,9-trioxadecane (15 and 16), and 1-(2'-nitrophenoxy)- and 1-(4'-nitrophenoxy)-3,6,9,12-tetraoxatridecane (17 and 18), were confirmed by the independent preparation of these compounds using a modification of Joeger's method.We have invented a new nitrating system (trimethylsilyl nitrate and BF3OEt2) and have shown that the selectivity (o/p ratio of nitrated products) is unusually high in CCl4.