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Krespan CG, Dixon DA. Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl. J Org Chem. 1998;63(1):36-43doi: 10.1021/jo970805y.
Krespan, C. G., & Dixon, D. A. (1998). Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl. The Journal of organic chemistry, 63(1), 36-43. https://doi.org/10.1021/jo970805y
Krespan, Carl G., and Dixon, David A.. "Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl." The Journal of organic chemistry vol. 63,1 (1998): 36-43. doi: https://doi.org/10.1021/jo970805y
Krespan CG, Dixon DA. Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl. J Org Chem. 1998 Jan 09;63(1):36-43. doi: 10.1021/jo970805y. PMID: 11674040.
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J Org Chem. 1998 Jan 09;63(1):36-43. doi: 10.1021/jo970805y.

Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl.

The Journal of organic chemistry

Carl G. Krespan, David A. Dixon

Affiliations

  1. Environmental Molecular Sciences Laboratory, Pacific Northwest National Laboratory, P.O. Box 999 K1-83, Richland, Washington 99352.

PMID: 11674040 DOI: 10.1021/jo970805y

Abstract

Adducts of primary F-alkyl iodides with nickel carbonyl are formed readily in donor solvents and pyrolyze at 100-150 degrees C to give olefinic coupling products in high yield. The mechanism proposed to account for the observed chemistry involves preferential alpha-elimination of fluorine with formation of a carbenoid species complex coordinated to nickel. Differences in reaction paths among several types of substrate halides are rationalized on the basis of polarization of the Ni-C bond in the adducts. Support for these proposals is provided by state-of-the-art calculations.

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