Synthesis of substituted phenanthrenes via intramolecular condensation based on temperature-dependent deprotonation using a weak carbonate base
K Monsieurs, G Rombouts, P Tapolcsanyi, P Matyus…
Index: Monsieurs, Katrien; Rombouts, Geert; Tapolcsanyi, Pal; Matyus, Peter; Maes, Bert U. W. Synlett, 2006 , # 19 p. 3225 - 3230
Full Text: HTML
Citation Number: 6
Abstract
Clearly, the deprotonation of the methyl group is the crucial step in the abovementioned reaction sequences. Not unexpectedly, all three research groups used a strong base to accomplish this deprotonation since the pK a value of the benzylic methyl protons is very high. However, the use of strong (and often nucleophilic) bases imposes a serious limitation on the functional group compatibility. We reasoned that the acidity should be greatly influenced by the chosen ...
Related Articles:
Ferrocenyl iminophosphine ligands in Pd-catalysed Suzuki couplings
[Teo, Shihui; Weng, Zhiqiang; Hor, T.S. Andy Journal of Organometallic Chemistry, 2011 , vol. 696, # 17 p. 2928 - 2934]
[Iwasawa, Tetsuo; Kamei, Toshinori; Watanabe, Satoshi; Nishiuchi, Masaki; Kawamura, Yasuhiko Tetrahedron Letters, 2008 , vol. 49, # 52 p. 7430 - 7433]
[Subhas, Madavu Salian; Racharlawar, Shailesh S.; Sridhar; Kennady, P. Kavin; Likhar, Pravin R.; Kantam, Mannepalli Lakshmi; Bhargava, Suresh K. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 13 p. 3001 - 3006]