Durch Bromierung ausgelöste Umlagerung tertiärer Allylalkohole : Der Einfluß eines Fluor-Substituenten auf Reaktionsgeschwindigkeit und Reaktionsverlauf
1980
Abstract
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)]
Details
Title
Durch Bromierung ausgelöste Umlagerung tertiärer Allylalkohole : Der Einfluß eines Fluor-Substituenten auf Reaktionsgeschwindigkeit und Reaktionsverlauf
Author(s)
Nagakura, Isao ; Savary, Dang Ngoc Hue ; Schlosser, Manfred
Published in
Helvetica Chimica Acta
Volume
63
Issue
5
Pages
1257-63
Date
1980
ISSN
0018-019X
Keywords
Rearrangement (in bromination of trimethylpentenol); Bromination; Kinetics of bromination (of trimethylpentenol and fluoro or Me derivs.); Stereochemistry (regioselectivity; in bromination of trimethylpentenol); bromination trimethylpentenol rearrangement regioselectivity; pentenol trimethyl bromination rearrangement
Note
CAN 93:238648
22-9
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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)
22-9
Physical Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03