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Cover Picture: Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid (Angew. Chem. Int. Ed. 30/2019)
Author(s) -
Nishikawa Keisuke,
Morita Kengo,
Hashimoto Subaru,
Hoshino Akihiro,
Ikeuchi Takumi,
Kumagai Momochika,
Morimoto Yoshiki
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201907848
Subject(s) - tetrahydropyran , tetrahydrofuran , aqueous solution , chemistry , cascade , epoxide , stereochemistry , ring (chemistry) , solvent , organic chemistry , chromatography , catalysis
The epoxide‐opening cascade cyclization of polyepoxides, which produces tetrahydrofuran (THF) in acidic aqueous media, produces tetrahydropyran (THP) in neutral water, as shown by K. Nishikawa, Y. Morimoto, and co‐workers in their Communication on page 10168 ff. A railway junction is used to illustrate the switching of polyepoxide cyclization modes. The trolley splash on the right side represents the formation of THP by heating polyepoxides in neutral water.