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85050328347
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In related reactions, alcohols can be oxidized to the corresponding aldehydes and ketones; see: (j) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Am. Chem. Soc. 1966, 88, 2328.
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2442554722
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note
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Although it is known that Lewis acids catalyze the ene-type reaction in "path c", catalyzed reactions have not been reported in "path d".
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25
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2442487530
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2.
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2442615748
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note
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The reaction of substrates having slow conversion rate provides varying amounts of the corresponding hydrazodicarboxylate. (entries n, o) than that of the parent benzaldehyde (entry m). In case of 4-dimethylamino benzaldehyde (entry 1),
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27
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2442483454
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note
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The dependency of the extent of inhibition on the amount of the radical scavenger used in the reaction was pointed out by a reviewer.
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28
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2442584244
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note
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Duplicates of both the uncatalyzed and catalyzed reactions were run at 0, 1.0, 2.5, 5.0, and 10 mol % of the scavenger, 4,4′ -dithiobis-(2,6-di-tert-butylphenol), neat and in 0.2 M solution in EtOAc. The progression of the reaction was monitored by 1H NMR spectroscopy. The details of this experiment are described in the Supporting Information.
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31
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0346208460
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(c) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
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0035929999
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Ishii, Y.4
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(e) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363.
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Lusztyk, J.5
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0031004405
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Chatgilialoglu, C.1
Ferreri, C.2
Luarini, M.3
Venturini, A.4
Zavitsas, A.A.5
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The intramolecular trapping experiments of 5-hexenoyl radical derived from 5-hexenal and azodicarboxylate both with and without catalyst were also carried out. In both cases, the formation of 2-methyl cyclopentanone derivative was not observed; instead, only the normal coupled product (7b/7b′) was isolated in good yield.
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