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A Facile Synthesis of Dinitro[2.2]metacyclophane and Its Partial Reduction

✍ Scribed by Tsuge, Akihiko ;Moriguchi, Tetsuji ;Mataka, Shuntaro ;Tashiro, Masashi

Book ID
102368239
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
250 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Both aromatic rings in [2.2]metacyclophanes(MCPs) can be easily nitrated in good yields by using the HNO~3~/dichloromethane system under mild conditions. This facile method is clearly superior to the nitration by strong nitrating agents such as nitronium tetrafluoroborate. Partial reduction of dinitro[2.2]MCP (2a) affords the intriguing aminonitro[2.2]MCP (3) which is one of the ultimate models of intramolecular charge‐transfer interaction. Compound 3 shows a significant bathochromic shift due to through‐space interaction between two aromatic rings.

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