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Silver‐Catalyzed Cyclization of Acetylenic Alcohols: Synthesis of Functionalized 2‐Methylene‐oxolanes
Author(s) -
Pale Patrick,
Chuche Josselin
Publication year - 2000
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/(sici)1099-0690(200003)2000:6<1019::aid-ejoc1019>3.0.co;2-4
Subject(s) - chemistry , catalysis , methylene , stoichiometry , intramolecular force , organic chemistry , solvent , polymer chemistry , combinatorial chemistry
Silver salts which have a basic counter‐ion are efficient catalysts for the regiospecific intramolecular addition of various acetylenic alcohols. Silver carbonate in aromatic solvent proved to be the best catalyst. Alkynols in which the two reacting parts of the molecule are relatively close together in space required only catalytic amounts of silver ion, while others cyclize readily with stoichiometric quantities. This heterocyclization reaction provides a mild and convenient access to 2‐methylene‐oxolanes or oxanes.