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Journal of Organometallic Chemistry | 1965

Halomethyl-metal compounds : I. Preparation of phenyl(trihalomethyl)mercury compounds

Dietmar Seyferth; James M. Burlitch

Abstract Detailed procedures for the preparation of C 6 H 5 HgCCl 3 , C 6 H 5 HgCCl 2 Br, C 6 H 5 HgCClBr 2 and C 6 H 5 HgCBr 3 by the Reutov-Lovtsova method are given. Evidence is presented which indicates that the reaction of phenylmercuric halide, haloform and potassium tert -butoxide forms C 6 H 5 HgCX 3 by way of nucleophilic displacement of halide ions from mercury by the trihalomethyl anion.


Journal of Organometallic Chemistry | 1967

Halomethyl-metal compounds X. The reaction of organosilicon, organogermanium and organotin hydrides with phenyl(trihalomethyl)mercury compounds☆

Dietmar Seyferth; James M. Burlitch; Hadwig Dertouzos; Harry D. Simmons

Abstract The reaction of phenyl(trihalomethyl)mercury compounds, C6H5HgCX2Br (X=Cl and Br), with organosilicon and organogermanium hydrides in benzene at 80° results in insertion of CCl2 and CBr2, respectively, into the Si—H and Ge—H bonds to give Si—CX2H and Ge—CX2H compounds. Triethylgermane was found to be four times more reactive than triethylsilane, and triethylsilane was 0.8 times as reactivate as cyclohexene. Evidence was obtained which suggest that dihalocarbenes (free or complexed) are involved as intermediates in these reactions. Tri-n-butyltin hydride reduced the C-Br bond of C6H5HgCX2Br mercurials, and C6H5HgCCl2H, C6H5HgCClBrH and C6H5HgCBr2H were prepared and characterized. However, this is not a practical preparative route to these mercurials.


Journal of the American Chemical Society | 1965

Halomethyl-Metal Compounds. II. The Preparation of gem-Dihalocyclopropanes by the Reaction of Phenyl(trihalomethyl)mercury Compounds with Olefins1

Dietmar Seyferth; James M. Burlitch; Richard J. Minasz; Jeffrey Yick-Pui. Mui; Harry D. Simmons; Arno J. H. Treiber; Susan R. Dowd


Journal of the American Chemical Society | 1967

Halomethyl-Metal Compounds. XII.1 The Action of Sodium Iodide on Phenyl(trihalomethyl)mercury Compounds. A New Method of Dihalocarbene Generation

Dietmar Seyferth; Michael E. Gordon; Jeffrey Yick-Pui. Mui; James M. Burlitch


Journal of the American Chemical Society | 1965

A New Method of Dihalocarbene Generation Based on Trihalomethylmetal Compounds

Dietmar Seyferth; Jeffrey Yick-Pui. Mui; Michael E. Gordon; James M. Burlitch


Journal of the American Chemical Society | 1963

The Preparation of Dihalomethyl Derivatives of Carbon, Silicon, and Germanium by the Action of Phenyl-(trihalomethyl)mercurials on C-H, Si-H, and Ge-H Linkages

Dietmar Seyferth; James M. Burlitch


Journal of the American Chemical Society | 1967

Halomethyl-metal compounds. XIV. Mechanism of the phenyl(bromodichloromethyl)mercury-olefin reaction

Dietmar Seyferth; Jeffrey Yick-Pui. Mui; James M. Burlitch


Journal of Organic Chemistry | 1962

Communication to the Editor: A New Preparation of Dihalocarbenes by an Organometallic Route

Dietmar Seyferth; James M. Burlitch; James K. Heeren


Journal of the American Chemical Society | 1969

Ionic dissociation of some compounds containing covalent metal-metal bonds

James M. Burlitch


Journal of the American Chemical Society | 1967

Crystal and molecular structure of Zn[Co(OC)4]2

Byungkook. Lee; James M. Burlitch; James L. Hoard

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Dietmar Seyferth

Massachusetts Institute of Technology

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Jeffrey Yick-Pui. Mui

Massachusetts Institute of Technology

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Michael E. Gordon

Massachusetts Institute of Technology

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Harry D. Simmons

Massachusetts Institute of Technology

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Hadwig Dertouzos

Massachusetts Institute of Technology

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James K. Heeren

Massachusetts Institute of Technology

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Stephen S. Washburne

Massachusetts Institute of Technology

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