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Deantiaromatization as a Driving Force in an Electrocyclic Reaction
Author(s) -
Harmata Michael,
Zheng Pinguan,
Schreiner Peter R.,
NavarroVázquez Armando
Publication year - 2006
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.200503812
Subject(s) - triethylamine , electrocyclic reaction , scheme (mathematics) , chemistry , computational chemistry , computer science , photochemistry , combinatorial chemistry , organic chemistry , mathematics , ring (chemistry) , mathematical analysis
But how does it smell? Theory and experiment support the notion that “deantiaromatization” can serve as a driving force in the 8‐π‐electron electrocyclization of a cyclopentadienone (see scheme; TEA=triethylamine; TFE=trifluoroethanol). The reaction proceeds in synthetically useful yields and could be applicable to the synthesis of the antiviral agent hamigeran B.