Highly selective methyl transfer from methylsilanes to phenylthallium(III) crown ether complexes

Fumitoshi Kakiuchi, Kiyonori Furuta, Shinji Murai, Yoshikane Kawasaki

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Reactions of (18-crown-6)phenylthallium(III) diperchlorate monohydrate (1a) with Me3SiR (R = PhCH2, Et, Ph, CH=CH2, SiMe3, OSiMe3) proceeded at 60°C to provide (18-crown-6)phenylmethylthallium-(III) perchlorate (3) in good to excellent yields. Cleavage of the Me-Si bond in tetramethylsilane using 1a also occurred at 25°C, albeit for a long reaction time. The silicon-containing products of the reaction of 1a with benzyltrimethylsilane were siloxanes. Intramolecular trapping of the silyl fragment by a hydroxy group using (1,7-DTC)phenylthallium(III) bis(trifluoromethane-sulfonate) (1b) was employed with trans-2-((trimethylsilyl)methyl)-1-cyclohexanol, affording a bicyclic silyl ether in 92% yield.

Original languageEnglish
Pages (from-to)15-16
Number of pages2
JournalOrganometallics
Volume12
Issue number1
Publication statusPublished - 1993
Externally publishedYes

Fingerprint

Crown Ethers
ethers
Cyclohexanols
Siloxanes
siloxanes
Silicon
perchlorates
sulfonates
reaction time
Ether
cleavage
trapping
fragments
methylidyne
silicon
products
18-crown-6
fluoroform
tetramethylsilane
perchlorate

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Highly selective methyl transfer from methylsilanes to phenylthallium(III) crown ether complexes. / Kakiuchi, Fumitoshi; Furuta, Kiyonori; Murai, Shinji; Kawasaki, Yoshikane.

In: Organometallics, Vol. 12, No. 1, 1993, p. 15-16.

Research output: Contribution to journalArticle

Kakiuchi, Fumitoshi ; Furuta, Kiyonori ; Murai, Shinji ; Kawasaki, Yoshikane. / Highly selective methyl transfer from methylsilanes to phenylthallium(III) crown ether complexes. In: Organometallics. 1993 ; Vol. 12, No. 1. pp. 15-16.
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