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Stereochemistry of Nucleophilic Substitution at Cyclo‐propanediazonium Ions
Author(s) -
Kirmse Wolfgang,
Engbert Theodor
Publication year - 1979
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197902281
Subject(s) - sn2 reaction , nucleophilic substitution , deamination , substitution (logic) , chemistry , walden inversion , ion , stereochemistry , substitution reaction , inversion (geology) , leaving group , medicinal chemistry , organic chemistry , geology , philosophy , catalysis , paleontology , linguistics , structural basin , enzyme
Model studies on S N 2 substitution in cyclopropanes show that inversion occurs in the “normal case”—at least in compunds having N 2 as leaving group. Thus, (1) reacts with configurational inversion to give (2) (4%) alongside the allyl compound (3) . The reason for the retention observed in special cases, e.g. on deamination of (4) , is probably a partly opened cation such as (5) .