Helicene Dianions: Paratropicity of Twisted Phenanthrene Dianions | Zendy

Frim Ron | Zendy; Mannschreck Albrecht | Zendy; Rabinovitz Mordecai | Zendy

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Helicene Dianions: Paratropicity of Twisted Phenanthrene Dianions

Author(s) -

Frim Ron,

Mannschreck Albrecht,

Rabinovitz Mordecai

Publication year - 1990

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.199009191

Subject(s) - phenanthrenes , helicene , chemistry , phenanthrene , alkyl , proton nmr , twist , proton magnetic resonance , crystallography , planar , lithium (medication) , stereochemistry , nuclear magnetic resonance , molecule , organic chemistry , physics , geometry , medicine , mathematics , endocrinology , computer graphics (images) , computer science

Non‐planar, alkyl‐substituted phenanthrenes are reduced to the dianions 1a–c with metallic lithium and sodium in [D 8 ] THF . The paratropic chemical shifts in the 1 H ‐ NMR spectrum and the linewidths of the signals of all dianions depend in the same way on the angle of twist: the greater the twist, the better the resolution of the 1 H ‐ NMR signals and the smaller the upfield shifts.

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