Synthesis and conformational analysis of halo [n. 3.1] propellanes

…, LAM Turkenburg, WH De Wolf…

Index: Jenneskens, L. W.; Turkenburg, L. A. M.; Wolf, W. H. de; Bickelhaupt, F. Recueil des Travaux Chimiques des Pays-Bas, 1985 , vol. 104, # 6 p. 184 - 190

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Abstract

Abstract A general synthesis of tetra-, tri-and dihalosubstituted propellanes is described starting from 1, 2-dimethylenecycloalkanes 2 to which dichlorocarbene is added to give the expected mono-addition products 3. Flash vacuum thermolysis of 3 gave the dichlorocyclopentenes 4; addition of dichloro-or dibromocarbene to 4 gave the tetrahalo [n. 3.1] propellanes 1. The tetrachloropropellane 1c was reduced, with one equivalent of ...