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CCDC 736469 (p-bromophenyl carbamate 12) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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CCDC 736469 (p-bromophenyl carbamate 12) 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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The isomeric O-carboxymethylated compound was also isolated as a minor product (20% yield) in this reaction
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The isomeric O-carboxymethylated compound was also isolated as a minor product (20% yield) in this reaction.
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22
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CCDC 736468 (diol 16) contains the supplementary crystallo-graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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CCDC 736468 (diol 16) contains the supplementary crystallo-graphic 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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24
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70349955015
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The corresponding decarboxymethylation compound (1,4-dike- tone 18 a, not shown) was also observed as a side product in this reaction. The likely formation of imine moieties at the two carbonyl sites of substrate 18 is reversible under the reaction conditions (i.e. H2O), thus allowing the eventual generation of the product (i.e. 1b). An alternative mechanism may involve initial attack of NH3 at the C2' carbonyl group and subsequent ring closure.
-
The corresponding decarboxymethylation compound (1,4-dike- tone 18 a, not shown) was also observed as a side product in this reaction. The likely formation of imine moieties at the two carbonyl sites of substrate 18 is reversible under the reaction conditions (i.e. H2O), thus allowing the eventual generation of the product (i.e. 1b). An alternative mechanism may involve initial attack of NH3 at the C2' carbonyl group and subsequent ring closure.
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