2736-73-4Relevant articles and documents
Preparation of (Z)-1,2-dichloroalkenes from terminal alkynes
Zhou, Ningzhang,Wang, Qiang,Lough, Alan J.,Yan, Hongbin
experimental part, p. 625 - 630 (2012/08/08)
(Z)-1,2-Dihaloalkenes are thermodynamically disfavoured of the two stereoisomers. This paper reports the synthesis of some (Z)-1,2-dichloroalkene analogues from mucochloric acid. A more versatile approach involved the chloroboration of terminal alkynes to yield corresponding (Z)-chloroboronic acid as a first step. Treatment of the organoboronic acid with potassium hydrogen difluoride followed by tetrabutylammonium trichloride gave (Z)-1,2- dichloroalkenes in moderate to good yields in a stereospecific manner.
Chemical and Biological Oxidation of Organohalides. Peracid Oxidation of Alkyl Iodides
Macdonald, Timothy L.,Narasimhan, N.,Burka, Leo T.
, p. 7760 - 7765 (2007/10/02)
The peracid oxidation of seven alkyl iodides has been examined in nonpolar solvents.The stoichiometry for the reaction is shown to be (8 + n)ArCO3H + 6RI + 3H2O -> (8 + n)ArCO2H + 6ROH + 2I2 + I2O5 + (n/2)O2 (R = n-heptyl, Ar = m-ClC6H4, n = 4-16).Evidence is presented for the intermediacy of an alkyliodosyl compound in these oxidations.Primary alkyl iodides give exclusively displacement products, whereas secondary iodides give a mixture of products resulting from displacement, elimination, and α-carbon oxidation.Tertiary iodides give products resulting form displacement and elimination.Mechanisms for the formation of these products are presented.The overall rate of peracid mediated reaction is dependent upon the alkyl group: tertiary > secondary > methyl primary iodides.The bioactivation of organohalides via an analogous halogen oxidation process is discussed.
Halogenated esters of phosphorus-containing acids (III)
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, (2008/06/13)
This invention deals with new phosphorus-containing esters having the formula STR1 wherein R represents a divalent hydrocarbon radical containing 1-20 carbon atoms; R' represents X, hydrogen or R"; R" represents a monovalent hydrocarbon radical containing 1-20 carbon atoms; and X represents chlorine or bromine. These new esters are useful particularly as fire retardants, agricultural chemicals, fuel additives, plasticizers, monomers and intermediates for the synthesis of other useful derivatives.
Unsaturated ester-amides of halogenated alkenes
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, (2008/06/13)
This invention deals with new unsaturated ester-amides of α,β-unsaturated polycarboxylic acids derived from halogenated alcohols of the formula EQU1 wherein R is a divalent hydrocarbon moiety having at least one and no more than 10 carbon atoms, X is a member selected from the class of bromine and chlorine, and R' is a member selected from the class of hydrogen and a monovalent hydrocarbon containing at least one and no more than 20 carbon atoms. Typical ester-amides are the maleates, fumarates, itaconates and citraconates. These monomers possess fire-retardant properties and are useful for the synthesis of polymers and copolymers.