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3 was used as the base, no reaction occurred, with the substrate recovered in almost quantitative yield. When NaOH was used, a few faint spots were detected by TLC, but no desired product was observed.
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3 was used as the base, no reaction occurred, with the substrate recovered in almost quantitative yield. When NaOH was used, a few faint spots were detected by TLC, but no desired product was observed.
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Based on the fact that more than 2.0 equiv of amine was required to drive the reaction to completion (Table 1, entry 3), it was concluded that the amine substitution may occur prior to the imine hydrolysis.
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Based on the fact that more than 2.0 equiv of amine was required to drive the reaction to completion (Table 1, entry 3), it was concluded that the amine substitution may occur prior to the imine hydrolysis.
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In all cases, a strong base e.g, sodium hydride, n-butyllithium, lithium diisopropylamide, etc, was used. For an example with a weak base such as aliphatic primary amines, see ref 10, in which the double EWG-activated 1,3-dithiolane moiety was fragmented upon heating to 120°C. For the fragmentation of 1,3-dithioles, see: Ogurtsov, V. A, Rakitin, O. A, Rees, C. W, Smolentsev, A. A, Belyakov, P. A, Golovanov, D. G, Lyssenko, K. A. Org. lett. 2005, 7, 791-794
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