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Lithium Benzocyclobuteneoxide as a Precursor of a Vinylogous Enolate: Solvent‐Controlled Synthesis of Highly Functionalized Seven‐Membered Benzocarbocycles
Author(s) -
Barluenga José,
GarcíaGarcía Patricia,
FernándezRodríguez Manuel A.,
Aguilar Enrique,
Merino Isabel
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501468
Subject(s) - lithium (medication) , solvent , diethyl ether , chemistry , carbene , ether , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , psychology , psychiatry
The reaction of alkynyl Fischer carbene complexes with the ortho ‐quinodimethane obtained from lithium benzocyclobuteneoxide leads to the preparation of highly functionalized seven‐membered benzocarbocycles (see scheme). The position and the nature of the functional groups in the product are solvent controlled: benzocycloheptenones are selectively formed in THF, whereas benzocycloheptene ketals are exclusively synthesized in diethyl ether.