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Unexpected Rearrangement Leading to Formation of a 1,3‐Bis(triphenylphosphonio)prop‐1‐en‐3‐idyl Carboxylate
Author(s) -
Aitken R. Alan,
Cleghorn Lee P.,
Leitch Rebecca M.,
Morrill Louis C.,
Slawin Alexandra M. Z.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000143
Subject(s) - chemistry , carboxylate , biphenyl , medicinal chemistry , stereochemistry , crystal structure , crystallography , organic chemistry
Whereas biphenyl‐4,4′‐dicarbonyl dichloride reacts with methylenetriphenylphosphorane to give the expected bis(acylylide) 1 , the same reaction of biphenyl‐2,2′‐dicarbonyl dichloride results in a multistep rearrangement leading to the zwitterionic 2‐[1,3‐bis(triphenylphosphonio)prop‐1‐en‐3‐id‐2‐yl]biphenyl‐2′‐carboxylate 2 . X‐ray crystal structures of both 1 and 2 are reported.