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Regioselectivity in S N H Reactions of Nitroquinolines with Chloromethyl Phenyl Sulfone
Author(s) -
Grzegożek Maria,
Woźniak Marian,
van der Plas Henk C.
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960426
Subject(s) - chemistry , carbanion , regioselectivity , adduct , sulfone , nitro , medicinal chemistry , nucleophile , substitution reaction , nucleophilic substitution , organic chemistry , catalysis , alkyl
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.