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Several cleverly designed conjugate additions to enones have trapped the presumed intermediates by employing internal radical traps. The yields of trapped product are typically in the range of 5-10% and in some cases the radical is unable to be intercepted: (a) Sarandeses, L. A, Mourino, A, Luche, J.-L. J. Chem. Soc, Chem. Commun. 1992, 798
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Several cleverly designed conjugate additions to enones have trapped the presumed intermediates by employing internal radical traps. The yields of trapped product are typically in the range of 5-10% and in some cases the radical is unable to be intercepted: (a) Sarandeses, L. A.; Mourino, A.; Luche, J.-L. J. Chem. Soc, Chem. Commun. 1992, 798.
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Ultrasonic irradition was deleterious in contrast to reactions with less highly substituted enones: Luche, J. L.; Allavena, C.; Petrier, C.; Dupuy, C. Tetrahedron Lett. 1988, 29, 5373.
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23644440971
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The related addition to ethyl vinyl sulfone affords a 2:1 ratio of cyclopentylmethyl and hexenyl addition: Zhao, M. M.; Qu, C.; Lynch, J. E. J. Org. Chem. 2005, 70, 6944.
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The related addition to ethyl vinyl sulfone affords a 2:1 ratio of cyclopentylmethyl and hexenyl addition: Zhao, M. M.; Qu, C.; Lynch, J. E. J. Org. Chem. 2005, 70, 6944.
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57
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34548731391
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Related radical probes with enones and enoates similarly imply radicaloid intermediates and in one instance intramolecular cyclization onto a pendant alkyne occurs in 10% yield.18
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18
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1642326585
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Blanchard, P.; Da Silva, A. D.; El, Kortbi, M. S.; Fourrey, J.-L.; Machado, A. S.; Robert-Gero, M. J. Org. Chem. 1993, 58, 6517.
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62
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34548722197
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After the reaction the octagonal stir bar is noticeably concave as a result of the abrasive action of silica on the Teflon coating
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After the reaction the octagonal stir bar is noticeably concave as a result of the abrasive action of silica on the Teflon coating.
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63
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0000576324
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Le Questel, J. Y.; Berthelot, M.; Laurence, C. J. Phys. Org. Chem. 2000, 13, 347.
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34548796588
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Unpublished X-ray analysis of the material indicated that the material is not a copper hydride: ref 18, footnote 7.
-
Unpublished X-ray analysis of the material indicated that the material is not a copper hydride: ref 18, footnote 7.
-
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70
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0000411019
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Stahl, R.; Jung, C.; Lutz, H. D.; Kockelmann, W.; Jacobs, H. Z. Anorg. Allg. Chem. 1998, 624, 1130.
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73
-
-
34548805960
-
-
2 reference code 01-089-0138; zinc metal reference code 01-087-0713, CuI reference code 01-083-1107.
-
2 reference code 01-089-0138; zinc metal reference code 01-087-0713, CuI reference code 01-083-1107.
-
-
-
-
74
-
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34548759153
-
-
The Cu(K) peak appears because the sample is adhered to a double-sided conductive carbon tape
-
The Cu(K) peak appears because the sample is adhered to a double-sided conductive carbon tape.
-
-
-
-
75
-
-
34548725650
-
-
3Zn reference code 03-065-6567.
-
3Zn reference code 03-065-6567.
-
-
-
-
76
-
-
34548717109
-
-
Transmission electron miscroscopy coupled with EDS failed to locate individual copper particles
-
Transmission electron miscroscopy coupled with EDS failed to locate individual copper particles.
-
-
-
-
79
-
-
85010592651
-
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For a related cyclization to an angular nitrile-containing cis-hydrindane see: Sato, M.; Suzuki, T.; Morisawa, H.; Fujita, S.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1987, 35, 3647. The cis-hydrindane stereochemistry was secured by hydrolysis to the corresponding amide and spectral correlation with a previously characterized sample: Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
-
For a related cyclization to an angular nitrile-containing cis-hydrindane see: Sato, M.; Suzuki, T.; Morisawa, H.; Fujita, S.; Inukai, N.; Kaneko, C. Chem. Pharm. Bull. 1987, 35, 3647. The cis-hydrindane stereochemistry was secured by hydrolysis to the corresponding amide and spectral correlation with a previously characterized sample: Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
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15444369069
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Fleming, F. F.; Zhang, Z.; Liu, W.; Knochel, P. J. Org. Chem. 2005, 70, 2200.
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82
-
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34548802495
-
-
1H NMR analysis of the crude reaction mixture failed to identify any of the diastereomeric cis-decalin.
-
1H NMR analysis of the crude reaction mixture failed to identify any of the diastereomeric cis-decalin.
-
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-
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83
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34548712441
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b (a) Spanenburg, W. J.; Snell, B. E.; Su, M.-C. Microchem. J. 1993, 47, 79.
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b (a) Spanenburg, W. J.; Snell, B. E.; Su, M.-C. Microchem. J. 1993, 47, 79.
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