Reactivity increase of dienophiles by change of the ester substituents into the acid chlorides: cycloaddition reaction of the diacid chloride of 3,10-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarboxylic acid with quadricyclane

作者: Davor Margetić , Anamarija Briš , Ronald N. Warrener , Douglas N. Butler

DOI: 10.1016/J.TET.2013.06.057

关键词:

摘要: Abstract Conversion of the ester substituents on cyclobutene π-bond dimethyl tricyclo[4.2.1.0 2,5 ]nona-3,7-diene-3,4-dicarboxylate to corresponding acid chloride increases cycloaddition reactivity toward quadricyclane so dramatically that reaction temperature can be dropped from 180 °C (preparation title 3,10-diester) room 3,10-diacid chloride). The cycloadduct product, an ring system, is extremely docile and recrystallized unchanged hot methanol.

参考文章(11)
Joel F. Liebman, Arthur Greenberg, Strained organic molecules ,(1978)
Stanley J. Cristol, The synthesis of quadricyclenes : A retrospective look Tetrahedron. ,vol. 42, pp. 1617- 1619 ,(1986) , 10.1016/S0040-4020(01)87578-5
Michael N. Paddon-Row, Evangelo Cotsaris, Harish K. Patney, The synthesis of rigid norbornylogs for the purpose of studying orbital interactions through bonds Tetrahedron. ,vol. 42, pp. 1779- 1788 ,(1986) , 10.1016/S0040-4020(01)87597-9
Davor Margetić, Douglas N. Butler, Ronald N. Warrener, Yasujiro Murata, Domino Diels–Alder reactions of N-methoxyethyl-7-oxa-norbornadiene-2,3-dicarboximide: an elusive, highly reactive dienophile Tetrahedron. ,vol. 67, pp. 1580- 1588 ,(2011) , 10.1016/J.TET.2010.12.032
Ronald N. Warrener, Shudong Wang, Richard A. Russell, The synthesis of U-shaped cavity molecules with “inner-surface” functionality Tetrahedron. ,vol. 53, pp. 3975- 3990 ,(1997) , 10.1016/S0040-4020(97)00013-6
Ronald N. Warrener, Ian G. Pitt, Douglas N. Butler, The synthesis of new linear and angular systems useful as rigid rods and spacers in the design of molecules Journal of the Chemical Society, Chemical Communications. pp. 1340- 1342 ,(1983) , 10.1039/C39830001340
Jürgen Sauer, Hubert Wiest, Albrecht Mielert, Eine Studie der DIELS-ALDER-Reaktion, I. Die Reaktivität von Dienophilen gegenüber Cyclopentadien und 9.10-Dimethyl-anthracen Chemische Berichte. ,vol. 97, pp. 3183- 3207 ,(1964) , 10.1002/CBER.19640971129
Claibourne D. Smith, Cycloaddition Reactions of “Quadricyclanes”1 Journal of the American Chemical Society. ,vol. 88, pp. 4273- 4274 ,(1966) , 10.1021/JA00970A038