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Spectroscopic study of 3‐methyl‐2,4‐diphenyl‐3‐azabicyclo[3.3.1]nonan‐9‐α(β)‐ols
Author(s) -
Iriepa I.,
GilAlberdi B.,
Galvez E.
Publication year - 1992
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.5570290239
Subject(s) - chemistry , nonane , ring (chemistry) , cyclohexane , nuclear magnetic resonance spectroscopy , cyclohexane conformation , stereochemistry , bicyclic molecule , spectroscopy , computational chemistry , organic chemistry , molecule , hydrogen bond , physics , quantum mechanics
3‐Methyl‐2,4‐diphenyl‐3‐azabicyclo[3.3.1]nonan‐9‐α(β)‐ols have been synthesized and studied by ir, 1 H and 13 C nmr spectroscopy. In deuteriochloroform and perdeuteriobenzene solutions, these compounds adopt a flattened chair‐chair conformation in which the cyclohexane ring is more flattened. From the 1 H and 13 C nmr data, several stereoelectronic effects have been deduced. The complete and unambiguous assignment of all protons of the 3‐azabicyclo[3.3.1]nonane system, not described up to date, has been carried out.