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Cycloaddition of P−C Single Bonds: Stereoselective Formation of Benzo‐1,3,6,2‐trioxaphosphepine Complexes via a Ditopic van der Waals Complex
Author(s) -
Malik Payal,
Espinosa Ferao Arturo,
Schnakenburg Gregor,
Streubel Rainer
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201606264
Subject(s) - van der waals force , stereoselectivity , chemistry , cycloaddition , stereochemistry , computational chemistry , molecule , organic chemistry , catalysis
While phosphaalkenes and phosphanes are known to participate in [4+ n ] cycloaddition reactions, P−C single bonds are inert in this respect. Herein, reactions of oxaphosphirane complexes with tetrachloro‐ ortho ‐benzoquinone are presented that reveal a stereoselective reaction of the endocyclic P−C bond to afford benzo‐1,3,6,2‐trioxaphosphepine complexes. High‐level DFT calculations provide evidence that the final product is derived from a sequence of three consecutive steps involving a ditopic van der Waals complex.