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Cracking Cavitands: Metal‐Directed Scission of Phosphinyl‐Substituted Resorcinarenes
Author(s) -
Chavagnan Thierry,
Sémeril David,
Matt Dominique,
Harrowfield Jack,
Toupet Loïc
Publication year - 2015
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.201500177
Subject(s) - cracking , chemistry , bond cleavage , metal , polymer chemistry , organic chemistry , catalysis
Resorcinarene‐derived tetramethylene cavitands bearing a diphenylphosphino group grafted to their wider rim undergo facile, directed CO bond breaking upon reaction with transition‐metal ions in the presence of nucleophiles. One possible reaction mechanism involves formation of a P , O ‐chelate complex, which weakens the adjacent OCH 2 bond, leading to the formation of an oxacarbenium intermediate.