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Synthesis of Heterocycles by Tandem Reactions: Beckmann Rearrangements/Allylsilane Cyclizations
Author(s) -
Schinzer Dieter,
Bo Yunxin
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199106871
Subject(s) - beckmann rearrangement , chemistry , oxime , ring (chemistry) , tandem , hydride , stereochemistry , medicinal chemistry , cascade reaction , organic chemistry , catalysis , hydrogen , materials science , composite material
The reaction behavior of functionalized oximes such as 1 is decisively influenced by the position of the N ‐hydroxyl group. Thus the ( Z )‐isomer reacts in the presence of diisobutylaluminum hydride to give the azepane 2 , while the ( E )‐isomer gives the perhydroquinoline 3 . Apparently, during the formation of 2 a Beckmann rearrangement first takes place with ring expansion, whereas in the case of 3 the oxime N atom is inserted directly into the ring that is being formed.