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Concave reagents, 6. Can the structure of concave reagents determine selectivities?
Author(s) -
Lüning Ulrich,
Schillinger Fritz
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901231021
Subject(s) - nitronate , chemistry , protonation , reagent , pyridine , medicinal chemistry , bicyclic molecule , stereochemistry , nitro , ion , organic chemistry , alkyl
The concave position of the proton in protonated concave pyridines 8 ·H + or 9 ·H + leads to increased selectivities in protonation reactions of nitronate anions 2a–d . Thus, the reprotonation of the nitronate anion 2a by the protonated concave pyridine 8 ·H + selectively yields the nitro compound 1a whereas the nitronate anions 2b–d are transformed to the Net products 4b–d .