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0036003278
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The chemisry of 7-azanorbornene derivatives has also been reviewed in the context of the synthesis of epibatidine. See
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Regarding the [2+2] cycloaddition of chlorosulfonylisocyanate to olefins the reaction appears to proceed via a concerted mechanism rather than a stepwise process, see
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3=Me) was described. In this case the reaction was achieved with diphenylacetylene and hence not regioselectivity is possible
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3=Me) was described. In this case the reaction was achieved with diphenylacetylene and hence not regioselectivity is possible.
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76
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0036295825
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Other synthetically useful reactions of oxa- and azabenzonorbornadienes derivatives catalyzed by Ni complexes have been recently reported. See, for instance
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Other synthetically useful reactions of oxa- and azabenzonorbornadienes derivatives catalyzed by Ni complexes have been recently reported. See, for instance: Rayabarapu, D. K.; Cheng, C. H. Pure & Appl. Chem. 2002, 74, 69.
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For recent reports on Ni-catalyzed [2+2+2] cyclotrimerizations of oxa-and azanorbornadienes, see
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For recent reports on Ni-catalyzed [2+2+2] cyclotrimerizations of oxa-and azanorbornadienes, see: Sambaiah, T.; Li, L. P.; Huang, D. J.; Rayabarapu, D. K.; Cheng, C. H. J. Org. Chem. 1999, 64, 3663.
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For recent reports on the Ru-catalyzed [2+2] cycloaddition reactions to norbornene derivatives, see
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A report of the Ru-catalyzed [2+2] cycloaddition (cyclopropanation) of 7-oxanorbornene 42 and propargyl alcohol 133 catalyzed by the complex 134 has been reported (Scheme 38). The reaction affords a mixture of cyclopropanes 135 and 136 in ratio 135: 136=6: 1. See
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Generally speaking, the control of the regioselectivity in the additions or cycloaddition reactions to the endocycclic double bond of a remote-substituted bicyclic system is an old question not yet well explained. For instance, some electrophilic additions show total regioselectivity depending on the nature of the remote substituent. In contrast, cycloaddition reactions such as 1,3-dipolar, Diels-Alder and Pauson-Khand have different levels of regioselectivity depending on both the remote substituent and the nature of the reagent involved in the reaction. These questions will be discussed in a next article of this serie
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Generally speaking, the control of the regioselectivity in the additions or cycloaddition reactions to the endocycclic double bond of a remote-substituted bicyclic system is an old question not yet well explained. For instance, some electrophilic additions show total regioselectivity depending on the nature of the remote substituent. In contrast, cycloaddition reactions such as 1,3-dipolar, Diels-Alder and Pauson-Khand have different levels of regioselectivity depending on both the remote substituent and the nature of the reagent involved in the reaction. These questions will be discussed in a next article of this serie.
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0343776189
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Arjona, O.; Csaky, A. G.; Murcia, M. C.; Plumet, J. J. Org. Chem. 1999, 64, 9739.
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All regioisomeric products were obtained as a diastereomeric E/Z mixture. In order to avoid complications in the determination of the regioselectivity the purified reaction mixtures were submitted to catalytic hydrogenation. As this last reaction was held in all cases with yields between 93-100 % the determination of the ratio of hydrogenated isomers may be consider as a convenient measurement of the regioselectivity of the reaction
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All regioisomeric products were obtained as a diastereomeric E/Z mixture. In order to avoid complications in the determination of the regioselectivity the purified reaction mixtures were submitted to catalytic hydrogenation. As this last reaction was held in all cases with yields between 93-100 % the determination of the ratio of hydrogenated isomers may be consider as a convenient measurement of the regioselectivity of the reaction.
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Weeresakare, G. M.; Liu, Z.; Rainier, J. D. Org. Lett. 2004, 6, 1625.
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The influence of the remote substituents in the sequence ROM-CM reactions has also been considered in the case of 8-oxabicyclo[3.2.1]octane derivatives. See
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The influence of the remote substituents in the sequence ROM-CM reactions has also been considered in the case of 8-oxabicyclo[3.2.1]octane derivatives. See: Whright, D. L.; Usher, L. C.; Jimenez, M. E. Org. Lett. 2001, 3, 4275.
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Usher, L. C.; Jimenez, M. E.; Ghiviriga, I.; Whright, D. L. Angew. Chem., Int. Ed. 2002, 41, 4560.
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