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1-(Trimethylsilyl)but-2-ene (or allyltrimethylsilane, ATMS) is an alkenylsilane compound that undergoes olefin metathesis catalyzed by WCl6 without requiring a co-catalyst, though the reaction exhibits an induction period. The catalytic process involves allyl-group transfer from silicon to tungsten, forming ClSiMe3 as a byproduct. The addition of Lewis acids like AlCl3 or AlBr3 eliminates the induction period and enhances both reaction activity and stereoselectivity, suggesting their involvement in the initiation, propagation, and termination steps of the metathesis mechanism.

18292-28-9

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18292-28-9 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 18292-28-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,2,9 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 18292-28:
(7*1)+(6*8)+(5*2)+(4*9)+(3*2)+(2*2)+(1*8)=119
119 % 10 = 9
So 18292-28-9 is a valid CAS Registry Number.

18292-28-9Relevant academic research and scientific papers

OLEFIN METATETHESIS OF ALKENYLTRIMETHYLSILANES

Berglund, Mats,Andersson, Carlaxel,Larsson, Ragnar

, p. C15 - C17 (1985)

WCl6 has been used as a catalyst for the metathesis of various alkenylsilanes and the degree of conversion found to be dependent on the distance between the olefinic bond and the silyl group.The first observation of metathetical conversion of allyltrimethylsilane in the absence of a co-catalyst is reported.

OLEFIN METATHESIS OF ALKENYLSILANES. II. ON THE INITIATION OF OLEFIN METATHESIS WITH ORGANOSILANES

Berglund, Mats,Andersson, Carlaxel,Larsson, Ragnar

, p. 61 - 74 (1986)

A study has been made of the cross-metathesis of alkenylsilanes CH2=CH(CH2)nSiX3 (n=1,2; X=CH3, Cl, OMe) with (Z)-2-pentene with WCl6 as the catalyst precursor.For allyltrimethylsilane (ATMS; n=1, X=CH3) the reaction proceeds without added co-catalyst but with an induction period.The catalytically-active intermediate in this case is formed by allyl-group transfer from Si to W, as revealed by the formation of ClSiMe3.Allyltrichlorosilane and allyltrimethoxysilane requires the addition of an alkylating co-catalyst, e.g.SnMe4.Addition of a Lewis acid, e.g.AlCl3 or AlBr3, show that for ATMS removes the induction period and substantially raises the activity.The initial activity and the E/Z-stereoselectivity are affected in a very similar way by the addition of the Lewis acid.The results indicate that the Lewis acid participates in the initiating, propagating, and terminating steps of the reaction.

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