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Difference in photochemical behavior in 3,6- and 2,5-di-tert-butyl-3H-azepine: The first photochemical bond formation between 2- and 6-position of 3H-azepine ring

✍ Scribed by Kyosuke Satake; Yuko Tawada; Shizuka Takami; Masaru Kimura

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 27 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390637

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✦ Synopsis

Abstract

Different photochemical behavior between 3,6‐ and 2,5‐di‐t‐butyl‐3__H__‐azepine was observed. The former gave wavelength dependent products 3,5‐di‐t‐butylpyridine on irradiation through Pyrex filter via photolysis and 4,7‐di‐t‐butyl‐2‐azabicyclo[3.2.0]hepta‐2,6‐diene on irradiation through quartz filter via photo‐isomerization. Meanwhile, 2,5‐di‐t‐butyl derivative gave exclusively a labile 2,5‐di‐t‐butyl‐6‐azabicyclo‐[3.2.0]hepta‐2,6‐diene on irradiation through Pyrex filter via hitherto unknown photoisomerization mode of the bond formation between 2‐ and 6‐position of the ring.

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