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Structural Studies of Crystalline Enamines
Author(s) -
Brown Kevin L.,
Damm Lorenz,
Dunitz Jack D.,
Eschenmoser Albert,
Hobi Reinhard,
Kratky Christoph
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610839
Subject(s) - enamine , chemistry , morpholine , piperidine , nitrogen atom , derivative (finance) , crystal structure , stereochemistry , organic chemistry , group (periodic table) , catalysis , financial economics , economics
Crystal structure analyses of five crystalline enamines together with recently published structural data for two other enamines reveal varying degree of pyramidality at the enamine nitrogen atom. The pyramidality appears to be most pronounced in enamines from piperidine and morpholine, less so in enamines derived from prolinoid amines. A pyrolidine enamine obtained from a derivative of cyclohexane‐1,4‐dione seems to have a virtually planar enamine group. The implications of these findings for current stereochemical problems in enamine chemistry are discussed.