H. Du, Ki Chul Park, Feng Wang
Nov 3, 2007
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4
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Journal
Organometallics
Abstract
The ferrocene derivatives (5−10) homoannularly disubstituted and heteroannularly trisubstituted by two different kinds of main-group elements, i.e., arsenic (As) and silicon (Si) or tin (Sn), were synthesized from N,N-dimethylaminomethylferrocene (1) and its diphenylarsino derivative 2 through mono- or dilithiation, followed by substitution with the organo-substituted chlorides RmMCln [R = alkyl, (m, n) = (2, 2) or (3, 1)] of main-group elements M = As, Si, or Sn. The dimethylaminomethyl (−CH2NMe2) group of the starting compounds facilitates lithiation of the cyclopentadienyl (Cp) ring and introduces lithium into the ortho-position of the −CH2NMe2 groups by the directing functionality. The efficiency of the subsequent substitution reaction with the organo-substituted chlorides RmMCln is influenced not only by their reactivity but also by the spatial factors of the main-group elements and the ferrocene derivative molecules to be reacted. All products 5−10 were identified by elemental analysis, proton nucle...