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Aspects of chirality in overcrowded bistricyclic enes
Author(s) -
Biedermann P. Ulrich,
Levy Amalia,
Stezowski John J.,
Agranat Israel
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070404
Subject(s) - chemistry , chirality (physics) , intramolecular force , folding (dsp implementation) , steric effects , bending , computational chemistry , plane (geometry) , crystallography , stereochemistry , geometry , quantum mechanics , physics , thermodynamics , chiral symmetry breaking , engineering , mathematics , nambu–jona lasinio model , electrical engineering , quark
Intramolecular overcrowding in bistricyclic enes ( 1 ) requires out‐of‐plane deformations in order to accommodate the sterically demanding tricyclic moieties without prohibitively close contacts of nonbonded atoms. The nonplanarity of 1 introduces the notion of chirality to the arena of overcrowded aromatic enes. Deviation from coplanarity occurs by twisting around the double bond and out‐of‐plane bending (hence pyramidalization ). The bending is realized by folding of the tricyclic moieties. The conformations of homomerous ( 1 , × = Y) and heteromerous ( 1 , × ≠ Y) bistricyclic enes and their mono‐ and disubstituted derivatives are analyzed along with their point group symmetries and chirality. The implications are illustrated using the structures of characteristic examples calculated with the semiempirical method PM3. © 1995 Wiley‐Liss, Inc.