130340-04-4Relevant academic research and scientific papers
PROCESS FOR PRODUCING 1,2-CIS-2-FLUOROCYCLOPROPANE-1-CARBOXYLIC ESTER COMPOUND
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Page/Page column 10, (2008/06/13)
Provided is an industrially applicable process for producing 1,2-cis-2-fluorocyclopropane-1-carboxylic ester. A process for producing a compound represented by formula (3): [wherein R 1 represents, for example, a C1-C8 alkyl group], which process includes reacting a compound represented by formula (1) : [wherein X 1 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 2 represents a hydrogen atom, a chlorine atom, a bromine atom, or an iodine atom; X 1 and X 2 are not simultaneously hydrogen atoms; and R 1 has the same meaning as defined in formula (3)] with a reducing agent represented by formula (2): €?€?€?€?€?€?€?€?M 1 BH m R 2 n (2-1) or M 2 (BH m R 2 n ) 2 €?€?€?€?€?(2-2) [wherein M 1 represents an alkali metal atom; M 2 represents an alkaline earth metal atom or a zinc atom; R 2 represents, for example, a hydrogen atom; m represents an integer from 1 to 4; n represents an integer from 0 to 3; and the sum of m and n is 4] in the presence of an aprotic polar solvent, and a Lewis acid such as a halide of an atom selected from among, for example, boron, magnesium, and aluminum.
Fluorinated cyclopropanecarboxylic acids and their derivatives
Gassen,Baasner
, p. 127 - 139 (2007/10/02)
The addition of halofluorocarbenes such as :CF2, :CClF or :CBrF, generated from the appropriate halofluoromethanes with bases, to butadiene or isoprene gives the corresponding l-vinyl substituted halofluorocyclopropanes in moderate to good yield. The vinyl group facilitates the carbene addition and permits a subsequent wide derivatisation. Several transformations including hydroboration, oxidation and Curtius degradation are presented. Furthermore, replacement of the chlorine atom in 2-chloro-2-fluorocyclopropanecarboxylic acid derivatives by hydrogen is achieved catalytically with Raney nickel. This sequence provides a convenient route to mono-fluorine substituted cyclopropane carboxylic acids.
