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. 2014 Aug 25;53(35):9380-3.
doi: 10.1002/anie.201403213. Epub 2014 Jul 15.

BN-phenanthryne: cyclotetramerization of an 1,2-azaborine derivative

Matthias Müller  1 , Cäcilia Maichle-Mössmer, Holger F Bettinger
Affiliations

BN-phenanthryne: cyclotetramerization of an 1,2-azaborine derivative

Matthias Müller et al. Angew Chem Int Ed Engl. .

Abstract

Thermolysis of 9-azido-9-borafluorene in heptane solution produces the tetramer of a BN-phenanthryne. The isolation of the self-trapping product provides evidence for the involvement of the BN-aryne in the thermolysis reaction. Its formation may be rationalized by denitrogenation of the azide and ring enlargement.

Keywords: arynes; azaborines; azides; reactive intermediates; thermolysis.

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