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Die Stereochemie der fragmentierenden Enthalogenierung von 1‐Chlor‐1‐fluor‐2‐(1‐halogenalkyl)cyclopropanen
Author(s) -
Spahić Bojana,
Schlosser Manfred
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630516
Subject(s) - chemistry , ring (chemistry) , halogenation , fluorine , halogen , chlorine , stereochemistry , double bond , regioselectivity , medicinal chemistry , crystallography , polymer chemistry , alkyl , organic chemistry , catalysis
The Stereochemistry of the Fragmentative Dehalogenation of 1‐Chloro‐1‐fluoro‐2‐(1‐halogenalkyl)cyclopropanes A number of model substrates were submitted to zinc‐promoted fragmentation, and the composition of the resulting mixture of isomeric fluorodienes was determined. The exocyclic reaction center, bearing the electrofugal leaving group, was found to undergo almost complete stereochemical randomization in the course of the reaction. On the other hand, the ring‐opening proceeds stereoselectively. The rotation, which brings the substitutents of the halogen‐free ring position into the plane of the new, fluorine‐bearing double‐bond, occurs mainly in that sense to move the electrons of the breaking ring linkage into the rear of the departing chlorine atom.