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Biradicaloid and Zwitterion Reactivity of Dicarbondiphosphide Stabilized with N‐Heterocyclic Carbenes
Author(s) -
Li Zhongshu,
Hou Yuanfeng,
Li Yaqi,
Hinz Alexander,
Chen Xiaodan
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705403
Subject(s) - chemistry , zwitterion , reactivity (psychology) , carbene , heteroatom , borane , lewis acids and bases , computational chemistry , molecule , delocalized electron , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry) , catalysis , medicine , alternative medicine , pathology
Organic biradicals are usually very short lived species under standard laboratory conditions, which makes their experimental studies difficult. In contrast, heteroatom‐substituted analogues of these biradicals show enhanced stability due to π‐electron delocalization, which is why main group biradicals (or biradicaloids) of archetypical heterocyclobutanediyls have been thoroughly investigated. Herein, N‐heterocyclic carbene (NHC)‐stabilized dicarbondiphosphide compounds of the type (L 2 )C 2 P 2 (L=NHC) were utilized to activate both single and multiple bonds in small molecules with a feasible concerted mechanism. This reactivity is explicable by considerable biradicaloid character of the dicarbondiphosphide compounds, which is further corroborated by theoretical studies. Furthermore, the dicarbondiphosphide compounds also exhibited Lewis base properties towards Lewis acids, such as borane and metal halides.