Synthesis and Absolute Configurations of Halogenoallenes

Cornelis J. Elsevier, Peter Vermeer, Aharon Gedanken, Wolfgang Runge

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77 Scopus citations

Abstract

The highly stereoselective synthesis of 3-methyl-1-halogenoallenes, 3-tert-butyl-1-halogenoallenes, and 1,3-ditert-butylallene is described. The R absolute configuration is assigned to the levorotatory halogenoallenes by relating them to allenes of known configurations. The configurational assignments are in agreement with (vacuum) circular dichroism data for the tert-butylallenes. The obtained results are used to clarify the hitherto existing confusion in the literature concerning absolute configurations of chloro and bromoallenes. Further, the signs and magnitudes of the ligand specific parameters for the halogens in the chirality functions approach, used to predict optical rotations of allenes, are discussed. The literature parameter for chlorine is revised and adequate numerical values for those of bromine and iodine are proposed.

Original languageEnglish
Pages (from-to)364-367
Number of pages4
JournalJournal of Organic Chemistry
Volume50
Issue number3
DOIs
StatePublished - Feb 1985

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