Regioselective Allylic Rearrangement of 3-Alkyl-N-allylindoles to 3-Alkyl-2-allylindoles

2016 ◽  
Vol 37 (9) ◽  
pp. 1533-1536
Author(s):  
Hye Ran Moon ◽  
Sangku Lee ◽  
Su Yeon Kim ◽  
Jae Nyoung Kim
Keyword(s):  
Allylic Rearrangement

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

Reactions of Phosphorus Pentachloride with Ethyl-, Vinyl-, and Ethynyl(trichloromethyl)carbinol and with 1,1,1-Trichloro-3-nonyn-2-ol

1973 ◽  
Vol 51 (12) ◽  
pp. 2017-2023 ◽  
Author(s):  
E. Wilkins Reeve ◽  
Thomas F. Steckel
Keyword(s):  
Vapor Phase ◽  
Acid Chloride ◽  
Phosphorus Pentachloride ◽  
Hydroxyl Group ◽  
Phosphate Ester ◽  
Allylic Rearrangement ◽  
Ethyl Vinyl ◽  
Normal Product

Reactions of phosphorus pentachloride with ethyl(trichloromethyl)carbinol (2), (trichloromethyl)-vinylcarbinol (7), ethynyl(trichloromethyl)carbinol (11a), and 1,1,1-trichloro-3-nonyn-2-ol (11b) have been studied. Whereas the reaction of phenyl(trichloromethyl)carbinol with phosphorus pentachloride leads to a nearly quantitative replacement of the hydroxyl group by chlorine, the reactions of the aliphatic (trichloromethyl)carbinols are more complicated. Thus the reaction of 2 with phosphorus pentachloride gave 18% of the normal product, 1,1,1,2-tetrachlorobutane (3), 13% of 1,1,2-trichloro-1-butene (4) from a dehydrohalogenation, and a higher boiling phosphate ester – acid chloride mixture. The alkynylcarbinols (11) gave tetrachlorobutynes (12) as well as tetrachloroallenes (13) by allylic rearrangement. A crystalline phosphate ester of 11a was also isolated. Several examples are given of catalytic rearrangements in the vapor phase of 1,1,1-trichloro-2-alkenes to 1,1,3-trichloro-1-alkenes.

Adducts of methyl ?,?-bis(trifluoromethyl)acrylate with nucleophiles and allylic rearrangement during their dehydrofluorination

1985 ◽  
Vol 21 (10) ◽  
pp. 1113-1116 ◽  
Author(s):  
I. V. Solodin ◽  
A. V. Eremeev ◽  
I. I. Chervin ◽  
R. G. Kostyanovskii
Keyword(s):  
Allylic Rearrangement
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