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A Stable Monocyclic 1,4‐Thiazepine: Synthesis and Characterization of 2,7‐Di‐ tert ‐butyl‐5‐methoxy‐1,4‐thiazepine
Author(s) -
Yamamoto Kagetoshi,
Yamazaki Shoko,
Osedo Hiroki,
Murata Ichiro
Publication year - 1986
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.198606351
Subject(s) - chemistry , sulfur , pyridine , beckmann rearrangement , benzene , ring (chemistry) , medicinal chemistry , contraction (grammar) , organic chemistry , oxime , medicine
Two tert ‐butyl groups adjacent to the sulfur atom in the title compound 1 hinder elimination of sulfur with ring contraction. Compound 1 can be obtained in a multistep reaction involving a Beckmann rearrangement and a Pummerer reaction. When 1 is heated in benzene in the presence of PPh 3 ring contraction takes place with formation of the pyridine 2 .