Durch Bromierung ausgelöste Umlagerung tertiärer Allylalkohole : Der Einfluß eines Fluor-Substituenten auf Reaktionsgeschwindigkeit und Reaktionsverlauf

Reaction of Me3CCMe(OH)CR:CH2 (I; R = H) with Br2 or NBS in aq. medium resulted in rearrangement, yielding ketones Me3CCOCHMeCH2Br and MeCOCR(CH2Br)CMe3 (III) and the oxirane II. With I (R = F, Me), bromination gave only ketone III. Competition expts. showed that I (R = F) underwent bromination at a much slower rate than I (R = H or Me). [on SciFinder (R)]


Published in:
Helvetica Chimica Acta, 63, 5, 1257-63
Year:
1980
Keywords:
Note:
CAN 93:238648
22-9
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0018-019X
written in German.
75-97-8 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with bromopropene); 111-25-1 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with fluoroiodopropene); 557-93-7 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with pinacolone); 124-11-8; 15870-10-7 Role: RCT (Reactant), RACT (Reactant or reagent) (bromination of, rate of); 5675-33-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Grignard reaction of, with hexyl bromide); 75681-84-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromination of, rate of); 75681-83-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromination of, rearrangement and); 3732-61-4P; 62927-00-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromination of, rearrangement in); 5675-31-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and iododehydroxylation of); 7432-56-6P; 7576-25-2P; 75681-86-6P; 75681-87-7P; 75681-88-8P; 75681-89-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 75681-85-5 Role: RCT (Reactant), RACT (Reactant or reagent) (ring cleavage of)
Laboratories:




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


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