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Regioselectivity in SNH Reactions of Nitroquinolines with Chloromethyl Phenyl Sulfone

✍ Scribed by Grzegożek, Maria ;Woźniak, Marian ;van der Plas, Henk C.

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
333 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

3‐Nitro‐, 4‐nitro‐, 7‐nitro‐, 5,7‐dinitro‐, and 6,8‐dinitroquinoline react with the carbanion of chloromethyl phenyl sulfone to give products of substitution of hydrogen at positions 4, 3, 8, 6,8, and 5,7, respectively. The reactions are found by quantum chemical calculations to be controlled by the interactions of the HOMO of the nucleophile with the LUMO of the substrate. The σ adducts 4‐(methylsulfonylphenyl)‐3‐nitroquinoline and 3‐(methylsulfonylphenyl)‐4‐nitroquinoline are detected by ^1^H‐NMR spectroscopy. In addition, heats of formation of the intermediary σ adducts 2a–d, f, h, and i are calculated.

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