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Synthesis and conformational analysis of isomeric 3‐propananilidotropanes
Author(s) -
Bagley Jerome R.,
Riley Thomas N.
Publication year - 1977
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.5570140412
Subject(s) - chemistry , piperidine , tropane , cyclohexane conformation , ring (chemistry) , stereochemistry , molecule , organic chemistry , hydrogen bond
The isomeric 3‐anilino and 3‐propananilidotropanes have been synthesized and obtained in isomerically pure form. The configurations and solute conformations of these isomers were studied via glc and nrar analysis. The 3β‐isomers have been shown to exist in the normal piper‐idine chair conformation whereas the 3α‐anilino tropane exists in a flattened piperidine chair conformation and the 3α‐propananilidotropane isomer preferentially exists in a conformation in which the piperidine ring system is a boat.