A novel class of alkylating reagent, RCu.BF3. Substitution of allyl halides with complete allylic rearrangement

1977 ◽  
Vol 99 (24) ◽  
pp. 8068-8070 ◽  
Author(s):  
Kazuhiro Maruyama ◽  
Yoshinori Yamamoto
Keyword(s):  
Allylic Rearrangement ◽  
Allyl Halides

Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives

2006 ◽  
Vol 71 (8) ◽  
pp. 1221-1228 ◽  
Author(s):  
Martin Klečka ◽  
Tomáš Tobrman ◽  
Dalimil Dvořák
Keyword(s):  
Double Bond ◽  
Magnesium Chloride ◽  
Allylic Rearrangement ◽  
Allyl Halides ◽  
Purine Ring

6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

Mechanistic Investigation of Rh(I)-Catalyzed Asymmetric Suzuki-Miyaura Coupling with Racemic Allyl Halides

2019 ◽  
Author(s):  
Lucy van Dijk ◽  
Ruchuta Ardkhean ◽  
Mireia Sidera ◽  
Sedef Karabiyikoglu ◽  
Özlem Sari ◽  
...  
Keyword(s):  
Quantum Chemical Calculations ◽  
Quantum Chemical ◽  
Experimental Studies ◽  
Mechanistic Investigation ◽  
Allyl Halides

A mechanism for Rh(I)-catalyzed asymmetric Suzuki-Miyaura coupling with racemic allyl halides is proposed based on a combination of experimental studies and quantum chemical calculations. <br>

Reaction of 1,4-dibromohexafluoro-2-butene with O- and N-nucleophiles

1988 ◽  
Vol 53 (3) ◽  
pp. 619-625 ◽  
Author(s):  
Ivan Hemer ◽  
Věra Moravcová ◽  
Václav Dědek
Keyword(s):  
Kinetic Study ◽  
Sodium Methoxide ◽  
Allylic Rearrangement ◽  
Rearrangement Product

Reaction of 1,4-dibromohexafluoro-2-butene (I) with sodium methoxide, ethoxide or isopropoxide in the corresponding alcohols proceeds with allylic rearrangement under formation of 3-alkoxy-4-bromohexafluoro-1-butenes II-IV. A kinetic study has proven the SN2’ mechanism for reaction of I with potassium phenoxide leading to 4-bromo-3-phenoxyhexafluoro-1-butene (V). Also the reaction of I with ammonia, affording 3-amino-4-bromo-2,4,4-trifluoro-2-butenenitrile (IX), is compatible with the allylic rearrangement by SN2’ mechanism. On the contrary, reaction of I with diethylamine gave no rearrangement product and, after hydrolysis, afforded N,N-diethyl-4-bromo-2,3,3,4,4-pentafluorobutanamide (XVI) and N,N-diethyl-4-bromo-2,3,4,4-tetrafluoro-2-butenamide (XVII) in the ratio 85:15.

Palladium Promoted Allylic Rearrangement Route to 6-Substitutbd 2-O-Acetyl-Hex-3-Enopyranosides

1988 ◽  
Vol 7 (1) ◽  
pp. 49-65 ◽  
Author(s):  
L. V. Dunkerton ◽  
K. T. Brady ◽  
F. Mohamed ◽  
B. P. McKillican
Keyword(s):  
Allylic Rearrangement

Evidence for a cytochrome P-450-catalyzed allylic rearrangement with double-bond topomerization

1988 ◽  
Vol 110 (6) ◽  
pp. 1979-1981 ◽  
Author(s):  
Robert H. McClanahan ◽  
Alain C. Huitric ◽  
Paul G. Pearson ◽  
John C. Desper ◽  
Sidney D. Nelson
Keyword(s):  
Double Bond ◽  
Allylic Rearrangement ◽  
Cytochrome P 450

scholarly journals Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guogang Deng ◽  
Shengzu Duan ◽  
Jing Wang ◽  
Zhuo Chen ◽  
Tongqi Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allyl Ether ◽  
Metal Catalyst ◽  
Metal Free ◽  
Allyl Ethers ◽  
Bond Forming ◽  
Allyl Halides ◽  
Synthetic Utility ◽  
Insight Into ◽  
Allyl Esters

AbstractAllylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

The Reactivity of Electrophilic Allyl Halides Towards Nucleophiles

2010 ◽  
Vol 91 (5) ◽  
pp. 430-430 ◽  
Author(s):  
R. Verhé ◽  
R. Thierie ◽  
D. Courtheyn ◽  
N. De Kimpe ◽  
L. De Buyck ◽  
...  
Keyword(s):  
Allyl Halides

Reaction of allyl halides with trichlorogermane

1960 ◽  
Vol 9 (11) ◽  
pp. 1920-1920
Author(s):  
V. F. Mironov ◽  
N. G. Dzhurinskaya ◽  
A. D. Petrov
Keyword(s):  
Allyl Halides
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