Formation of (vinyl-ferrocenyl)stibines involving beta-elimination: Hypervalent Sb-N bonding

Abstract

Unusual syntheses of vinyl substituted ferrocenylstibines viz. diphenyl(2-vinylferrocenyl) stibine (2) and iodo-(N, N-dimethylamino-ethylferrocenyl)(2-vinylferrocenyl)stibine (4) involving beta-elimination, are reported. Stibines Ph(2)SbFc (1) or FC2SbCl (3) containing dimethylaminoethyl-pendant arm on a ferrocenyl ring on reaction with MeI gives vinyl substituted ferrocenylstibines. All the new stibines were characterized by IR, mass, H-1, C-13, COSY, HETCOR NMR spectroscopy. The structures of all of these 1,2-disubstituted ferrocenylstibines were determined by X-ray diffraction analyses. The compounds 3 and 4 show hypervalent bonding between the antimony and nitrogen atoms giving 6 and 5 coordinated antimony, respectively. This is the first report on ferrocenylstibines containing a vinyl group in their framework. (c) 2007 Elsevier B.V. All rights reserved.