Cyclopentane formation in the reduction of 1,5-dihaloalkanes with a nickel(I) macrocycle

Journal Article · Wed Jun 01 00:00:00 EDT 1988 · Inorg. Chem.; (United States)

DOI:https://doi.org/10.1021/ic00284a037· OSTI ID:5688519

Ram, M S; Bakac, A; Espenson, J H

When the nickel(I) macrocycle, Ni(tmc)/sup +/, reacts with 1,5-dihalopentanes, X(CH/sub 2/)/sub 5/X (X = Br, I) cyclopentane is produced in nearly quantitative yield. The reaction scheme for the process is presented as follows: Ni (tmc)/sup +/ reacts with X(CH/sub 2/)/sub 5/X by an atom-transfer process to yield X(CH/sub 2/)/sub 4/CH/sub 2//sup 0/; this radical reacts with a second Ni(tmc)/sup +/ to yield the organometallic complex (tmc)Ni(CH/sub 2/)/sub 4/CH/sub 2/X/sup +/. Cyclopentane results from the ni(tmc)/sup +/-catalyzed decomposition of (tmc)Ni(CH/sub 2/)/sub 5/X/sup +/. 14 references, 1 table.

• Research Organization: Iowa State Univ., Ames (USA)
• DOE Contract Number: W-7405-ENG-82
• OSTI ID: 5688519
• Journal Information: Inorg. Chem.; (United States), Journal Name: Inorg. Chem.; (United States) Vol. 27:11; ISSN INOCA
• Country of Publication: United States
• Language: English

Related Subjects

090121* -- Hydrocarbon Fuels-- Chemical Synthesis-- (1976-1989)
10 SYNTHETIC FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
ALKANES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
COMPLEXES
CYCLOALKANES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
NICKEL COMPLEXES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SYNTHESIS
TRANSITION ELEMENT COMPLEXES