Die Stereochemie der fragmentierenden Enthalogenierung von 1-Chlor-1-fluor-2-(1-halogenalkyl)cyclopropanen

A no. of model substrates, e.g., I (X = Br, iodo) (anti/cis), were submitted to Zn-promoted fragmentation and the compn. of the resulting mixt. of isomeric fluorodienes was detd. The exocyclic reaction center, bearing the electrofugal leaving group, undergoes almost complete stereochem. randomization, while ring opening proceeds stereoselectively. The stereochem. results are related to changes in electron configuration occurring during the reaction. [on SciFinder (R)]

Published in:
Helvetica Chimica Acta, 63, 5, 1242-56
CAN 93:238647
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in German.
75-43-4 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with methylbutenyl acetate); 497-02-9; 19319-26-7 Role: RCT (Reactant), RACT (Reactant or reagent) (esterification of, with acetic anhydride); 7440-66-6 Role: USES (Uses) (fragmentation of chlorofluoro(haloalkyl)cyclopropanes in presence of, stereochem. and); 75681-77-5P; 75715-31-0P; 75715-32-1P; 75715-76-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and bromodehydroxylation of); 19248-94-3P; 41414-68-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and cycloaddn. reaction with dichlorofluoromethane); 75681-71-9P; 75681-72-0P; 75681-73-1P; 75715-22-9P; 75715-23-0P; 75715-24-1P; 75715-25-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and dehalogenation of, stereochem. of); 75681-74-2P; 75715-27-4P; 75715-28-5P; 75715-74-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 75681-75-3P; 75715-26-3P; 75715-29-6P; 75715-75-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydroxylation of); 75681-78-6P; 75715-35-4P; 75715-36-5P; 75715-77-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and reductive fragmentation of); 52021-24-6P; 52021-25-7P; 75681-76-4P; 75681-79-7P; 75681-80-0P; 75681-81-1P; 75681-82-2P; 75715-30-9P; 75715-33-2P; 75715-34-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)

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

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