Ring-fused gem-Dibromocyclopropanes as Precursors to

Martin G. Banwell; Robert W. Gable; Richard J. Greenwood; John N. Lambert; Maureen F. Mackay; Justine M. Walter

doi:10.1055/s-1997-933

Synlett 1997; 1997(8): 953-955
DOI: 10.1055/s-1997-933

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Ring-fused gem-Dibromocyclopropanes as Precursors to "Tunable" Molecular Clefts Possessing Convergent Functional Groups

Martin G. Banwell¹ , Robert W. Gable² , Richard J. Greenwood³ , John N. Lambert² , Maureen F. Mackay³ , Justine M. Walter²

¹Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia, FAX 61-6-249-5995; E-mail mgb@rsc.anu.edu.au
²School of Chemistry, The University of Melbourne, Parkville, Victoria 3052, Australia
³School of Chemistry, La Trobe University, Bundoora, Victoria 3052, Australia

Abstract

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Reaction of certain ring-fused gem-dibromocyclopropanes with methyllithium affords syn-cyclopropylidene dimers such as 2 which contain converging and potentially co-ordinating groups. Cyclofunctionalisation of the double bonds within these latter compounds allows the "angle-of-bite" between the co-ordinating groups to be "tuned" such that, under electrospray conditions in the mass spectrometer, derivative 7 forms a 1:1:1 complex with, for example, D-ribose and sodium ion.

gem-dibromocyclopropane - cyclopropylidene dimer - molecular cleft - monosaccharide - triangulane

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