Process for functionalizing alkanes

Bergman, R G; Janowicz, A H; Periana-Pillai, R A

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Title: Process for functionalizing alkanes

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Abstract

Process for functionalizing saturated hydrocarbons selectively in the terminal position comprises: (a) reacting said saturated hydrocarbons with a metal complex CpRhPMe/sub 3/H/sub 2/ in the presence of ultraviolet radiation at -60/sup 0/ to -17/sup 0/C to form a hydridoalkyl complex CpRhPMe/sub 3/RH; (b) reacting said hydridoalkyl complex with a haloform CHX/sub 3/ at -60/sup 0/ to -17/sup 0/C to form the corresponding haloalkyl complex of step (a) CpRhPMe/sub 3/RX; and (c) reacting said haloalkyl complex with halogen -60 to 25/sup 0/C to form a functional haloalkyl compound.

Inventors:: Bergman, R G; Janowicz, A H; Periana-Pillai, R A

Issue Date:: 1984-06-12

OSTI Identifier:: 6363796

Application Number:: ON: TI85006420

Assignee:: Dept of Energy

DOE Contract Number:: AC03-76SF00098

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ALKANES; DERIVATIZATION; HALOGENATION; HALOGENATED ALIPHATIC HYDROCARBONS; SYNTHESIS; CHEMICAL REACTIONS; CYCLOALKENES; PHOSPHINES; PHOTOCHEMICAL REACTIONS; RHODIUM COMPLEXES; ULTRAVIOLET RADIATION; ALKENES; COMPLEXES; ELECTROMAGNETIC RADIATION; HYDROCARBONS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; PHOSPHORUS COMPOUNDS; RADIATIONS; TRANSITION ELEMENT COMPLEXES; 400500* - Photochemistry

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                    Bergman, R G, Janowicz, A H, and Periana-Pillai, R A. Process for functionalizing alkanes.  United States: N. p., 1984. 
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                    Bergman, R G, Janowicz, A H, & Periana-Pillai, R A. Process for functionalizing alkanes.  United States.

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                    Bergman, R G, Janowicz, A H, and Periana-Pillai, R A. Tue .  
        "Process for functionalizing alkanes".  United States.

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@article{osti_6363796,

  title        = {Process for functionalizing alkanes},

  author       = {Bergman, R G and Janowicz, A H and Periana-Pillai, R A},

  abstractNote = {Process for functionalizing saturated hydrocarbons selectively in the terminal position comprises: (a) reacting said saturated hydrocarbons with a metal complex CpRhPMe/sub 3/H/sub 2/ in the presence of ultraviolet radiation at -60/sup 0/ to -17/sup 0/C to form a hydridoalkyl complex CpRhPMe/sub 3/RH; (b) reacting said hydridoalkyl complex with a haloform CHX/sub 3/ at -60/sup 0/ to -17/sup 0/C to form the corresponding haloalkyl complex of step (a) CpRhPMe/sub 3/RX; and (c) reacting said haloalkyl complex with halogen -60 to 25/sup 0/C to form a functional haloalkyl compound.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {1984},

  month        = {6}

}

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Process for functionalizing alkanes

Patent Bergman, R G; Janowicz, A H; Periana, R A

Process for functionalizing saturated hydrocarbons comprises: (a) reacting said saturated hydrocarbons of the formula: R[sub 1]H wherein H represents a hydrogen atom; and R[sub 1] represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRh[P(R[sub 2])[sub 3]]H[sub 2] wherein Cp represents a cyclopentadienyl or alkylcyclopentadienyl radical; Rh represents a rhodium atom; P represents a phosphorus atom; R[sub 2] represents a hydrocarbon radical; H represents a hydrogen atom, in the presence of ultraviolet radiation to form a hydridoalkyl complex of the formula: CpRh[P(R[sub 2])[sub 3]](R[sub 1])H (b) reacting said hydridoalkyl complex with an organic halogenating agent such asmore » « less
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Process for functionalizing saturated hydrocarbons selectively in the terminal position comprising: (a) reacting said saturated hydrocarbons of the formula: RH where: H represents a hydrogen atom, and R represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhPMe.sub.3 H.sub.2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, Me represents a methyl group, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60.degree. to -17.degree. C. to form a hydridoalkyl complex of the formula: CpRhPMe.sub.3 RH (b) reacting said hydridoalkyl complexmore » « less
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Process for functionalizing saturated hydrocarbons comprising: (a) reacting said saturated hydrocarbons of the formula: R.sub.1 H wherein H represents a hydrogen atom; and R.sub.1 represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRh[P(R.sub.2).sub.3 ]H.sub.2 wherein Cp represents a cyclopentadienyl or alkylcyclopentadienyl radical; Rh represents a rhodium atom; P represents a phosphorus atom; R.sub.2 represents a hydrocarbon radical; H represents a hydrogen atom, in the presence of ultraviolet radiation to form a hydridoalkyl complex of the formula: CpRh[P(R.sub.2).sub.3 ](R.sub.1)H (b) reacting said hydridoalkyl complex with an organic halogenating agent such as a tetrahalomethane or a haloform ofmore » « less
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