Ethylene formation in the reduction of 1,4-dihaloalkanes with a nickel(I) macrocycle

Journal Article · Tue Oct 27 23:00:00 EST 1987 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00256a075· OSTI ID:5648680

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

The nickel tetraaza macrocycle Ni(tmc)/sup +/ reacts with 1,4-dihaloalkanes (halide = Br, I) to produce ethylene, eq 1. No X-(CH/sub 2/)/sub 4/-X + 2Ni(tmc)/sup +/ ..-->.. 2XNi(tmc)/sup +/ + 2C/sub 2/H/sub 4/ (1) cyclobutane or butenes were observed by VPC under any conditions, although suitable controls were performed to show that they would have survived the reaction conditions. 1-Bromobutane and minor amounts of n-butane (2-10%) result only when a deficient quantity of Ni(tmc)/sup +/ is used. With excess Ni(tmc)/sup +/, however, both byproducts are largely eliminated, and ethylene is formed in > 90% yield.

• Research Organization: Iowa State Univ., Ames
• DOE Contract Number: W-7405-ENG-82
• OSTI ID: 5648680
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 109:22; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
BROMINATED ALIPHATIC HYDROCARBONS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
DATA
ETHYLENE
EXPERIMENTAL DATA
HALOGENATED ALIPHATIC HYDROCARBONS
HYDROCARBONS
INFORMATION
IODINATED ALIPHATIC HYDROCARBONS
NICKEL COMPOUNDS
NUMERICAL DATA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
REDUCTION
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS