- (Lig)Ni(0) induced preparation of mono- and dicarboxylic acids from cyclopentene and carbon dioxide
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Cyclopentene is shown to be an ideal substrate for coupling reactions with (Lig)nickel(0) systems. By variation of the ligands and addition of promoters, it is possible by successive application of carbon dioxide or carbon monoxide to prepare highly selectively series of cyclopentane- and cyclopentenecarboxylic acids (six examples), 4, 5, 6, 11, 14, 15, cyclopentanedicarboxylic acids (three examples), 7, 8, 12, or 2-hydroxycyclopentanecarboxylic acid (9) in good yields. The C5-skeleton is retained in the products.
- Hoberg,Ballesteros,Sigan,Jegat,Milchereit
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p. 395 - 398
(2007/10/02)
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- Stereo- and enantioselectivity in catalytic hydrogenolysis of chiral substituted ferrocenes to give cyclopentanes
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The catalytic hydrogenolysis of 1,2-disubstituted ferrocenes having planar chirality and functional groups such as carboxyl (including ester) or tertiary amino proceeds under mild conditions (1 atm of H2, Pd/C, CF3COOH, 50 deg C) with the retention of fun
- Sokolov, V. I.,Troitskaya, L. L.,Khrushcheva, N. S.,Reutov, O. A.
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p. 227 - 234
(2007/10/02)
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- Formylation and Acylation Reactions Catalysed by Trifluoromethanesulphonic Acid
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Regioselective formylation of toluene, m- and p-xylene, and mesitylene has been achieved by carbonylation in trifluoromethanesulphonic acid at CO pressures of 90-125 atm.In the case of cumene, the formylation reaction is in competition with disproportionation to form di- and tri-isopropylbenzenes, leading to a complex product mixture.Slow addition of cyclohexene or cyclopentene to a mixture of benzene and CF3SO3H under a high CO pressure affords 4-cyclohexylbenzaldehyde and 4-cyclopentylbenzaldehyde in 34percent and 33percent yieds, respectively, while 2-methylbut-1-ene gives 2,2,3-trimethylindanone (39percent) under similar conditions.When cyclohexene is mixed with the acid under carbon monoxide (120 atm) before addition of benzene the major products are cyclohexyl phenyl ketone and cyclohexenyl cyclohexyl ketones.
- Booth, Brian L.,El-Fekky, Teymour A.,Noori, Ghazi F. M.
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p. 181 - 186
(2007/10/02)
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