One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2

Synlett

Volumn , Issue 11, 1999, Pages 1769-1771

  Takai, Kazuhiko ^a   Hikasa, Shintaro ^a   Ichiguchi, Tetsuya ^a   Sumino, Naoki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

(E) 1 alkenylsilane; Chromium(II); Chromium(III); Geminal dichromium reagent; Geminal diiodo compound; Manganese

Indexed keywords

ALKENYL GROUP; CHROMIUM; IODINE DERIVATIVE; MANGANESE; REAGENT; SILANE DERIVATIVE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; REACTION ANALYSIS;

EID: 0032706458     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2948     Document Type: Article

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27. 4-Phenyl-1-iodo-1-butene (4) was reduced to 4-phenyl-1-butene (3) under the reaction conditions (25 °C, 24 h).
28. 3SiCl, and a catalytic amount of chromium(II) chloride at 25 °C for 24 h did not afford alkenylsilane 2; iodoalkene 4 was recovered in 66% yield along with alkene 3 in 20% yield. The result suggests that alkenylsilane 2 was not produced via reductive iodine-silicone exchange of iodoalkene 4.
29. 2 (Table 1). Chromium(III) hexahydrate (99.995% purity) was purchased from Aldrich Chemical Co. and dehydrated by treatment with thionyl chloride. Pray, A. R. Inorg. Synth. 1954, 5, 153.
30. The reaction was finished within 1 h at 25 °C.
31. 2 were in 7% and 79% yields, respectively.
32. Chromium(II) chloride (99.9% purity) was purchased from Aldrich Chemical Co.
33. Manganese powder was purchased from Kojundo Chemical Laboratory Co. (99.9% purity, -50 mesh). The powder was used for reactions without purification.