Syntheses of organofluorine compounds. VII. Structurally biased 2-fluoroallyl cations as generated (or not generated) in cyclopropane ring-opening reactions

The Ag ion-catalyzed ring-opening of a 1:4 mixt. of syn- and anti-cyclopropanes I and II gave the expected mixt. of CH2:CFC(OH)MeCMe3 and (Z)-MeC(CMe3):CFCH2OH in 56 and 19% yield, resp. Under similar conditions spiro analog. III underwent Wagner-Meerwein rearrangement to give bicycloheptane IV. Mechanism of the reactions are discussed. [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 60, 2, 590-7
Year:
1977
Keywords:
Note:
CAN 87:5127
22-6
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in English.
471-84-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with chlorofluorobornane); 62927-02-0P; 62961-02-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and rearrangement of); 62926-98-1P; 62926-99-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and solvolytic ring-opening reaction of); 62927-00-8P; 62927-01-9P; 62927-03-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 17455-13-9 Role: PRP (Properties) (reaction of dichlorofluoromethane with trimethylbutene in presence of); 3487-44-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with camphor); 594-56-9 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with dichlorofluoromethane in presence of hexaoxacyclooctadecane); 76-22-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with methanetriphenylphosphone); 75-43-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with trimethylbutene in presence of hexaoxacyclooctadecane)
Laboratories:




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