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Spontaneous resolution of 2,3‐bis‐fluoren‐9‐ylidenesuccinic acid induced by achiral guest inclusion
Author(s) -
Tanaka Koichi,
Iwamoto Toshimasa,
Wada ShinIchi,
Frelek Jadwiga,
Caira Mino R.
Publication year - 2006
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.20295
Subject(s) - chemistry , chirality (physics) , succinic anhydride , acetone , inclusion (mineral) , solid state , stereochemistry , inclusion compound , chloride , medicinal chemistry , organic chemistry , crystallography , molecule , mineralogy , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
The racemic title host compound ( 1 ) formed homochiral inclusion crystals (conglomerate) of 1 with acetone, while heterochiral inclusion crystals (racemate) were obtained when complexed with ethyl acetate. Upon treatment of the homochiral inclusion crystals of 1 with gaseous acetyl chloride in the solid state, optically active 2,3‐bis(fluorenylidene)succinic anhydride ( 3 ) was obtained in high optical purity. Chirality 18:483–488, 2006. © 2006 Wiley‐Liss, Inc.