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Frontispiece: Polar Organofluorine Substituents: Multivicinal Fluorines on Alkyl Chains and Alicyclic Rings
Author(s) -
O'Hagan David
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202083662
Subject(s) - vicinal , geminal , diastereomer , chemistry , alkyl , ring (chemistry) , fluorine , polar , molecule , alicyclic compound , hydrogen bond , aromaticity , stereochemistry , chemical polarity , side chain , crystallography , polymer chemistry , organic chemistry , physics , astronomy , polymer
This Review in organo‐fluorine chemistry outlines the synthesis and properties of compounds with multiple vicinal fluorinated alkyl chains and rings. Chain conformations of individual diastereoisomers with ‐CHF‐ at adjacent carbons are influenced by stereoelectronic factors associated with the polar C−F bond and also the polarised geminal hydrogens. Chains generally prefer a conformation which acts to minimise overall molecular polarity, and where the C−F bonds orient away from each other. However, when vicinal fluorines are positioned all‐cis on a ring, this results in an electronegative ‘fluorine face’ and an electropositive ‘hydrogen face’, and then these Janus face molecules become polarised and are highly crystalline. For the full story see the Review by D. O'Hagan on page 7981 ff.