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A Novel Domino Reaction: Cyclization of Alkynyl Sulfides by Reaction with IPy 2 BF 4
Author(s) -
Barluenga José,
Romanelli Gustavo P.,
AlvarezGarcía Lorenzo J.,
Llorente Isidro,
González José M.,
GarcíaRodríguez Esther,
GarcíaGranda Santiago
Publication year - 1998
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/(sici)1521-3773(19981204)37:22<3136::aid-anie3136>3.0.co;2-o
Subject(s) - intramolecular force , chemistry , substituent , domino , ring (chemistry) , intermolecular force , friedel–crafts reaction , cascade reaction , intramolecular reaction , coupling reaction , medicinal chemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , molecule
Formation of polycyclic structures within a few minutes: The intramolecular cyclization of diynes, activated by a benzenesulfenyl substituent, upon reaction with IPy 2 BF 4 proceeds as an efficient exo–endo coupling. A subsequent novel Friedel–Crafts‐like ring closure provides the product [Eq. (1)]. Thus, intra‐ and intermolecular cyclizations can be carried out.