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The benzoin condensation catalysis by bis(azolin‐2‐ylidene)s and bis(azolidin‐2‐ylidene)s and its interpretation within the context of nucleophilic carbene chemistry
Author(s) -
Castells J.,
LópezCalahorra F.,
Geijo F.,
PérezDolz R.,
Bassedas M.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230315
Subject(s) - chemistry , carbene , benzoin , nucleophile , salt (chemistry) , catalysis , context (archaeology) , condensation , organic chemistry , medicinal chemistry , paleontology , physics , thermodynamics , biology
The preparation of bis(thiazolin‐2‐ylidene)s by passing a methanol solution of the corresponding thiazolium salt through an ion exchange column (basic form) is reported and the use of these “dimers” as benzoin condensation catalysts is studied. The “dimers” show better catalytic activity than the corresponding thiazolium salt plus base. A general discussion of the benzoin condensation catalysis within the framework of nucleophilic carbene chemistry is carried out and as a result of it the important role played by the “dimers” is emphasized. Mechanistic suggestions related with this fact are put forward.