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Issue 10, 1975

Organosilicon chemistry. Part XIV. Insertion of 1,2,2-trifluoroethylidene into C–H bonds of tetra-alkylsilanes: a novel alkyl group rearrangement

Abstract

1,2,2-Trifluoroethylidene, generated by pyrolysis of trifluoro-(1,1,2,2-tetrafluoroethyl)silane, inserts (10–30%) into various C–H bonds in the alkyl groups of alkyltrimethylsilanes, RSiMe3(R = Et, Prn, Pri, Bun, Bui, Bus, isopentyl, and cyclopentyl), but does not insert into the primary C–H bonds in tetramethylsilane. The ease of insertion into the C–H bonds is tertiary > secondary > primary, and C–H bonds α to silicon are somewhat deactivated as compared with those further removed from silicon. In general the α-insertion products are unstable under the reaction conditions and decompose to give fluorotrimethylsilane; other insertion products are stable. Insertion is also observed into the primary C–H bonds of hexamethyldisilane and hexamethyldisiloxane (ca. 5%). A novel rearrangement of the s-butyl group to the n-butyl group occurs during the reaction of trichloro-(s-butyl)-silane with methylmagnesium bromide.

Article information


J. Chem. Soc., Perkin Trans. 1, 1975, 966-971
Article type
Paper

Organosilicon chemistry. Part XIV. Insertion of 1,2,2-trifluoroethylidene into C–H bonds of tetra-alkylsilanes: a novel alkyl group rearrangement

R. N. Haszeldine, A. E. Tipping and R. O. B. Watts, J. Chem. Soc., Perkin Trans. 1, 1975, 966 DOI: 10.1039/P19750000966

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