Premium
1,2‐Phosphaborines: Hybrid Inorganic/Organic P–B Analogues of Benzene
Author(s) -
Barnard Jonathan H.,
Brown Paul A.,
Shuford Kevin L.,
Martin Caleb D.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507003
Subject(s) - chemistry , delocalized electron , conjugated system , benzene , valence (chemistry) , ring (chemistry) , phosphine , photodissociation , aromaticity , oligomer , bond length , stereochemistry , crystallography , molecule , photochemistry , polymer chemistry , organic chemistry , catalysis , polymer
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 CB 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‐BPC 4 conjugated heterocycles and open a new avenue for BP as a valence isoelectronic substitute for CC in arene systems.