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NMR Spectroscopic Investigation of the Adducts Formed by Addition of Cuprates to Ynoates and Ynones: Alkenylcuprates or Allenolates?
Author(s) -
Nilsson Karolina,
Andersson Thomas,
Ullenius Christina,
Gerold Andreas,
Krause Norbert
Publication year - 1998
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/(sici)1521-3765(19981002)4:10<2051::aid-chem2051>3.0.co;2-f
Subject(s) - cuprate , adduct , alkyne , chemistry , simple (philosophy) , polymer chemistry , organic chemistry , philosophy , physics , epistemology , condensed matter physics , catalysis , superconductivity
Alkenylcuprates or allenolates–that is the question! The structures of the adducts formed by addition of cuprates to ynones and ynoates has been a matter of controversy for several decades. New NMR spectroscopic investigations with 13 C‐labeled substrates now reveal that there is no simple answer to the question. Some reactants give alkenylcuprates 1 , others allenolates 2 as the most stable adducts. The transformations can be regarded as carbocupration of an alkyne rather than a Michael addition.