ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
The Stereochemistry of the Fragmentative Dehalogenation of 1-Chloro-1-fluoro-2-(1-halogenalkyl)cyclopropanesA 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.
Zusätzliches Material:
3 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19800630516
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