Catalyst Effects on the Stereoselectivity of Addition of Tetrachloromethane to 1,3-Cyclohexadiene

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Title:Catalyst Effects on the Stereoselectivity of Addition of Tetrachloromethane to 1,3-Cyclohexadiene
Creators:
Hájek, Milan
Kotora, Martin
Adámek, František
Davis, Reg
Fischer, Cecile
Joshu, Warren A. C.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 5, pp. 774-777
Uncontrolled Keywords:Stereoselectivity, Addition, Ligand effects

Abstract

The stereoselectivity of addition reaction of tetrachloromethane with conjugate cyclodienes represented by 1,3-cyclohexadiene has been studied in respect to the type of catalyst. In all addition reactions the product of 1,4-addition, i.e. 1-chloro-4-(trichloromethyl)cyclohex-2-ene was formed exclusively consisting of two isomers (<strong>1a</strong>, <strong>1d</strong>). Copper-amine complexes gave higher isomeric ratio <strong>1a</strong> : <strong>1d</strong> (up to 3.7) than ruthenium complex (1.3) at the same conditions (80 °C). Moreover, it was found that isomeric ratio was temperature dependent and the highest value (6.4) was obtained at lower temperature (20 °C). The results proved both catalyst and ligand effects on stereoselectivity of addition reaction of conjugated cyclic dienes. This supports a non-chain reaction mechanism because isomeric ratios of chain reactions are catalyst independent.

Title:Catalyst Effects on the Stereoselectivity of Addition of Tetrachloromethane to 1,3-Cyclohexadiene
Creators:
Hájek, Milan
Kotora, Martin
Adámek, František
Davis, Reg
Fischer, Cecile
Joshu, Warren A. C.
Uncontrolled Keywords:Stereoselectivity, Addition, Ligand effects
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:5
Page Range:pp. 774-777
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960774UNSPECIFIED
ID Code:978
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Hájek, Milan; Kotora, Martin; Adámek, František; Davis, Reg; Fischer, Cecile; Joshu, Warren A. C. (1996) Catalyst Effects on the Stereoselectivity of Addition of Tetrachloromethane to 1,3-Cyclohexadiene. Collection of Czechoslovak Chemical Communications, 61 (5). pp. 774-777. ISSN 0010-0765

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