
Journal of Organic Chemistry p. 6656 - 6670 (2017)
Update date:2022-08-03
Topics:
Cowie, Thomas Y.
Veguillas, Marcos
Rae, Robert L.
Rougé, Mathilde
Zurek, Justyna M.
Prentice, Andrew W.
Paterson, Martin J.
Bebbington, Magnus W. P.
Nitrofurans undergo intramolecular Diels-Alder reactions with tethered electron-poor dienophiles more rapidly and in higher yield than non-nitrated furans. Computational studies indicate that increased stabilization of a partial positive charge on the nitro-substituted carbon in both transition state and product is the driving force for these reactions. Frontier molecular orbital energy differences indicate a switch from normal to inverse electron demand upon nitration. There does not appear to be a contribution from any differences in aromatic stabilization energy between furans and nitrofurans. Calculations show that the nitrofuran reactions proceed via a highly asynchronous transition state allowing easier bond formation between two sterically hindered carbons.
View MoreWuhan Soleado Technology Co.,Ltd.
Contact:86-2783341481 18971291927
Address:RM2405 Unit 1 Builing 1, Taiyin Tower, Changqing Road,Wuhan China
Contact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Contact:+86-10-83993285
Address:Rm.1708, Haobai Tower, Building 6, No.50, North Road, West Third Ring, Haidian District, Beijing, China
Contact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Hangzhou TJM Chemical Trade Co., Ltd
Contact:86-571-88223276 86-13388481653
Address:2221#,Boyuexuan,1860# Binsheng Road,Binjiang District, Hangzhou CityZhejiang Province, 310051, P. R. China
Doi:10.1016/j.bmcl.2016.01.071
(2016)Doi:10.1016/j.bmc.2005.10.008
(2006)Doi:10.1248/cpb.31.3309
(1983)Doi:10.1016/j.tetlet.2008.03.150
(2008)Doi:10.1002/anie.200502067
(2006)Doi:10.1055/s-2005-924769
(2006)