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For experimental details and characterization data for compounds 1-6, as well as labeling experiments, see the Supporting Information.
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For experimental details and characterization data for compounds 1-6, as well as labeling experiments, see the Supporting Information.
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70349683356
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Under these reaction conditions the reaction did not go to completion. Products 1g (9%) and N-tosylaniline (12%) were isolated by column chromatography. Longer reaction times caused decomposition. The use of microwave radiation did not result in any major improvement.
-
Under these reaction conditions the reaction did not go to completion. Products 1g (9%) and N-tosylaniline (12%) were isolated by column chromatography. Longer reaction times caused decomposition. The use of microwave radiation did not result in any major improvement.
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46
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For a review on carbophilic activation by π-acids
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3, although giving a lower yield than for gold-catalysis and is also accompanied by other side products. See the Supporting Information.
-
3, although giving a lower yield than for gold-catalysis and is also accompanied by other side products. See the Supporting Information.
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49
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0141451974
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3-induced Friedel-Crafts cyclization of 1,3-bis-exocyclic dienes leading to 4a-methyltetrahydrofluorenes
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70349681236
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See for instance the conversion of 1g into 3g. Also, minor amounts of 3 h were isolated from the gold-catalyzed reaction of 1h. figue presented
-
See for instance the conversion of 1g into 3g. Also, minor amounts of 3 h were isolated from the gold-catalyzed reaction of 1h. figue presented
-
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51
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3 in the presence of 2,4,6-tri-tertbutylpyrimidine (TTBP) supports this hypothesis. In this case, upon heating for 24 h in DCE, the reaction gives the corresponding diene 3a (25 %), which arises from a single cyclization rather the double cyclization product 2 a. For the use of TTBP in metal-catalyzed reactions
-
3 in the presence of 2,4,6-tri-tertbutylpyrimidine (TTBP) supports this hypothesis. In this case, upon heating for 24 h in DCE, the reaction gives the corresponding diene 3a (25 %), which arises from a single cyclization rather the double cyclization product 2 a. For the use of TTBP in metal-catalyzed reactions, see: T. Schwier, A.W. Sromek, D. M. L. Yap, D. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 9868-9878.
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5 was prepared by a cross-coupling reaction, see the Supporting Information.
-
-5 was prepared by a cross-coupling reaction, see the Supporting Information.
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-
-
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53
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70349683355
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After heating at 60°C for 40 min only compound 5 was present in the reaction mixture. By extending the reaction time to 1 h it allowed the identification of significant amounts of unchanged 5, although some decomposition was evident by TLC This trend was still noticed when heating lasted foe 3 or 7 h. After 24 h, only trace amounts of 5 were present, and a complex mixture was formed without any evidence for the formation of a type-2 product.
-
After heating at 60°C for 40 min only compound 5 was present in the reaction mixture. By extending the reaction time to 1 h it allowed the identification of significant amounts of unchanged 5, although some decomposition was evident by TLC This trend was still noticed when heating lasted foe 3 or 7 h. After 24 h, only trace amounts of 5 were present, and a complex mixture was formed without any evidence for the formation of a type-2 product.
-
-
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54
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70349687876
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CCDC 734150 (2m) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
-
CCDC 734150 (2m) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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