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Volumn 54, Issue 27, 2015, Pages 7823-7827

Diels-Alder Reactions of 1,2-Azaborines

Author keywords

aromaticity; azaborine heterocycles; boron; cycloaddition; synthetic methods

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; BORON; CHEMICAL REACTIONS;

EID: 85027922658     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201503483     Document Type: Article
Times cited : (43)

References (52)
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    • Ashe et al. reported the reaction of a B-Ph-1,2-dihydro-1,2-oxaborine with dimethylacetylenedicarboxylate (DMAD) that is consistent with a Diels-Alder reaction followed by an Alder-Rickert cleavage reaction. The corresponding B-Ph-1,2-azaborine was shown not to be reactive under the same conditions. See:, J. Chen, Z. Bajko, J. W. Kampf, A. J. Ashe, Organometallics 2007, 26, 1563-1564.
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    • reported attempts to observe Diels-Alder reactivity between BN-fused polyaromatic 1,2-azaborines with maleic anhydride. However, exclusively the starting material was recovered. See.
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    • Crystallographic data for 2a can be found in the Supporting Information. CCDC-1058889 (2a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • Crystallographic data for 2a can be found in the Supporting Information. CCDC-1058889 (2a) 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 DA adducts 2 are nonvolatile and are not amenable to purification using chromatography.
    • The DA adducts 2 are nonvolatile and are not amenable to purification using chromatography.
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    • Crystallographic data for 2h can be found in the Supporting Information (CCDC-1058890).
    • Crystallographic data for 2h can be found in the Supporting Information (CCDC-1058890).
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    • Crystallographic data for 2m can be found in the Supporting Information (CCDC-1058891).
    • Crystallographic data for 2m can be found in the Supporting Information (CCDC-1058891).


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