Reactions of a highly crowded cyclic stannylene with iodoalkanes, enones, and dienes. Inhibition of nucleophilic substitution at tin(IV) centers

Ashrafolmolouk Asadi, Colin Eaborn, Michael S. Hill, Peter B. Hitchcock, Michael M. Meehan, J. David Smith

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24 Citations (Scopus)

Abstract

The cyclic stannylene RSnR (2; RR = C(SiMe3)2SiMe2CH2CH2Me 2Si(Me3Si)2C) reacted with alkyl iodides R′I (R′ = Et, iPr) to give the SnIV compounds RSnR′IR (6b,c), which were converted by treatment with silver trifluoroacetate into RSnR′(OCOCF3)R (7b,c). Reaction of the stannylene 2 with appropriate enones or diones yielded the products RRSnOC(Et)=CHCH2 (10), RRSnOCPh=CPhO (11), RRSnOC6H2-3,5-tBu2O (12), and RRSnOC14H3O (13) (OC14H8O = 9,10-phenanthrenediolato). The crystal structures of 6b, 7b,c, and 10-13 have been determined. Treatment of 2 with water, alcohols, or phenol led to ring opening. There is evidence from ESR spectroscopy that the oxidative additions of diones involve radical intermediates. The compound RSnMeIR (6a) reacted with ICI to give the chloride RSnMeClR (15), but, in contrast to the previously described crowded trialkyltin halides (Me3Si)3CSnMe2X (X = Cl, I), neither 6a nor 15 reacted with nucleophilic reagents.

Original languageEnglish
Pages (from-to)2430-2437
Number of pages8
JournalOrganometallics
Volume21
Issue number12
DOIs
Publication statusPublished - 10 Jun 2002

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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