Syntheses of organofluorine compounds. VIII. Solvolytic ring-opening of alkoxychlorofluorocyclopropanes: a ready access to fluorinated a,b-unsaturated aldehydes and ketones

1-Chloro-1-fluorocyclopropanes [I; R, R1, R2, R3 = H, OMe, Me, Me; Me, OMe, H, H; H, OMe, Me, Me2CH(CH2)3; H, OMe, Me, Me2C:CHCH2CH2; Me, Me, H, MeOCH:CMeCH2CH2; H, OEt, H, Me] were easily prepd. by cycloaddn. of ClFC: to alkenyl ethers in a 2-phase system. I were solvolyzed by heating in an aq. solvent mixt. to give 2-fluoro-2-alkenals, which were readily reduced by LiAlH4 to the corresponding 2-fluoro-2-alkenols. [on SciFinder (R)]

Published in:
Helvetica Chimica Acta, 60, 5, 1739-46
CAN 87:133807
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in English.
927-53-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with fluorobutenone); 75-43-4 Role: PROC (Process) (conversion of, to chlorofluorocarbene and cyclocondensation with ethylenic ethers); 627-40-7; 4696-25-7; 4696-26-8; 17574-84-4; 63995-94-8; 63995-95-9; 63995-96-0; 63995-97-1 Role: RCT (Reactant), RACT (Reactant or reagent) (cyclocondensation of, with chlorofluoromethylene); 63995-90-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromination of); 2372-98-7P; 63995-82-4P; 63995-83-5P; 63995-84-6P; 63995-86-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 63995-76-6P; 63995-77-7P; 63995-78-8P; 63995-79-9P; 63995-80-2P; 63995-81-3P; 64031-53-4P; 64031-54-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and solvolysis of); 2356-08-3P; 3917-34-8P; 3917-35-9P; 25129-61-7P; 63995-85-7P; 63995-87-9P; 63995-88-0P; 63995-89-1P; 63995-91-5P; 63995-92-6P; 63995-93-7P; 63995-98-2P; 63995-99-3P; 64031-55-6P; 64103-21-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)

 Record created 2006-03-03, last modified 2018-01-27

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