Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5585-5588

  Longshaw, Alistair I ^a   Carland, Michael W ^a   Krenske, Elizabeth H ^a   Coote, Michelle L ^a   Sherburn, Michael S ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

Ab initio calculations; Radicals; Synthetic methods

Indexed keywords

ADAMANTANE DERIVATIVE; METHANE; ORGANOHALOGEN DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; TRIS(TRIMETHYLSILYL)METHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DEHALOGENATION; MATHEMATICAL ANALYSIS; REACTION ANALYSIS; REDUCTION; THERMODYNAMICS;

EID: 34447250002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.055     Document Type: Article

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25. No reaction was observed upon attempted initiation of the radical reaction with either AIBN or VAZO 88.
26. Experimental procedure: A solution of 1-bromoadamantane (20 mg, 0.09 mmol), anisole (10 μL), triethylsilane (150 μL, 0.9 mmol, 10 mol equiv), and/or tris(trimethylsilyl)methane (260 μL, 0.9 mmol, 10 mol equiv) in benzene (1 mL) was heated to 80 °C. A solution of benzoyl peroxide (50 mg, 0.2 mmol, 2 equiv) in benzene (1 mL) was added, via syringe pump, over 5 h. A diluted sample of the reaction mixture was injected directly into an Agilent 6850 series GC instrument fitted with an Agilent 19091 J-233E, HP5 5% phenyl methyl siloxane column (capillary size: 30.0 m × 250 μm × 1.00 μm).
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32. -1 (Table 1) is in good agreement with this experimental value
33. -1 (Table 1) is in good agreement with this experimental value
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36. There remains the possibility that a contaminant other than those tested here is facilitating the transformations described in the 2006 communication.