Premium
Stereochemistry and bonding in N ‐substituted‐2‐phenyl‐3‐cyanoaziridines
Author(s) -
Keifer Paul A.,
Nagel Donald L.,
Cromwell Norman H.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250201
Subject(s) - chemistry , aziridine , steric effects , ring (chemistry) , nitrile , stereoselectivity , stereochemistry , chemical shift , hyperconjugation , alkyl , benzonitrile , medicinal chemistry , molecule , organic chemistry , catalysis
A series of ten N ‐alkyl(aralkyl)‐2‐phenyl‐3‐cyanoaziridines has been synthesized to continue investigations of the molecular stereochemistry and bonding of functionalized aziridines. Substantial spectroscopic evidence is presented which indicates the presence of stereoselective hyperconjugation between the phenyl and nitrile groups and the aziridine ring. The 1 H and 13 C nmr chemical shifts are rationalized in terms of the interactions of the substituents on the aziridine ring, and how these interactions vary with the steric bulk of the nitrogen substituents. Various stereoselective coupling constants ( 1 H‐ 1 H and 13 C‐ 1 H) are also reported.