1,2-Phosphaborines: Hybrid Inorganic/Organic P-B Analogues of Benzene.

Angewandte Chemie (International ed. in English)

PubMedID: 26315985

Barnard JH, Brown PA, Shuford KL, Martin CD. 1,2-Phosphaborines: Hybrid Inorganic/Organic P-B Analogues of Benzene. Angew Chem Int Ed Engl. 2015;.
Photolysis of the cyclic phosphine oligomer [PPh]5 in the presence of pentaarylboroles leads to the formation of 1,2-phosphaborines by the formal insertion of a phenylphosphinidene fragment into the endocyclic C?B bond. The solid-state structure features a virtually planar central ring with bond lengths indicating significant delocalization. Appreciable ring current in the 1,2-phosphaborine core, detected in nuclear independent chemical shift (NICS) calculations, are consistent with aromatic character. These products are the first reported 1,2-BPC4 conjugated heterocycles and open a new avenue for B?P as a valence isoelectronic substitute for C?C in arene systems.