Residual Enantiomerism and Chromatographic Resolution of a 1,1,2‐Triarylalkene | Zendy

Biali Silvio E. | Zendy; Rappoport Zvi | Zendy; Mannschreck Albrecht | Zendy; Pustet Nikola | Zendy

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Residual Enantiomerism and Chromatographic Resolution of a 1,1,2‐Triarylalkene

Author(s) -

Biali Silvio E.,

Rappoport Zvi,

Mannschreck Albrecht,

Pustet Nikola

Publication year - 1989

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198901991

Subject(s) - enthalpy , isomerization , chemistry , ring (chemistry) , molecule , enantiomer , resolution (logic) , computational chemistry , analytical chemistry (journal) , chromatography , stereochemistry , organic chemistry , thermodynamics , physics , catalysis , artificial intelligence , computer science

A three‐ring flip A⇄B is the isomerization mechanism of lowest activation enthalpy for triarylalkene propeller molecules. NMR studies on 1 , for which this mechanism leads to a diastereomerization rather than an enantiomerization, gave a value of 79.5 kJ mol −1 for this process. After chromatographic separation of the enantiomers of 1 , it was also possible to determine the activation enthalpy of its enantiomerization, which presumably occurs by a [β,β′] two‐ring flip: 92.7 kJ mol −1 .

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