[1,3]-Sigmatropic Shift of an Allylic Chloride

Johannes Boshkow; Thomas Scattolin; Franziska Schoenebeck; Erick M. Carreira

doi:10.1002/hlca.201800148

[1,3]-Sigmatropic Shift of an Allylic Chloride

Helvetica Chimica Acta ◽

10.1002/hlca.201800148 ◽

2018 ◽

Vol 101 (12) ◽

pp. e1800148

Author(s):

Johannes Boshkow ◽

Thomas Scattolin ◽

Franziska Schoenebeck ◽

Erick M. Carreira

Keyword(s):

Sigmatropic Shift ◽

Allylic Chloride

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Direct acylamination of quinoline, isoquinoline, benzimidazole, pyridazine, and pyrimidine 1-oxides. Novel 1,5-sigmatropic shift

The Journal of Organic Chemistry ◽

10.1021/jo00889a009 ◽

1975 ◽

Vol 40 (1) ◽

pp. 41-47 ◽

Cited By ~ 29

Author(s):

R. A. Abramovitch ◽

R. B. Rogers ◽

G. M. Singer

Keyword(s):

Sigmatropic Shift

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C−N Bond Insertion of a Complexed Phosphinidene into a Bis(imine) − A Novel 2,3-Sigmatropic Shift

European Journal of Organic Chemistry ◽

10.1002/1099-0690(200206)2002:11<1797::aid-ejoc1797>3.0.co;2-x ◽

2002 ◽

Vol 2002 (11) ◽

pp. 1797-1802 ◽

Cited By ~ 4

Author(s):

Mark J. M. Vlaar ◽

Pieter Valkier ◽

Marius Schakel ◽

Andreas W. Ehlers ◽

Martin Lutz ◽

...

Keyword(s):

Sigmatropic Shift

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A thermally degenerate [1,9] sigmatropic shift

Journal of the Chemical Society D Chemical Communications ◽

10.1039/c29710000833 ◽

1971 ◽

pp. 833 ◽

Cited By ~ 7

Author(s):

K. P. Parry ◽

C. W. Rees

Keyword(s):

Sigmatropic Shift

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Thermal Claisen rearrangement studies on 4,6- and 2,4-diacetylresorcinol bisallyl ethers: observation of loss or [1,5] sigmatropic shift of acetyl groups

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19880000623 ◽

1988 ◽

pp. 623 ◽

Cited By ~ 5

Author(s):

Ammanamanchi S. R. Anjaneyulu ◽

Uppuluri V. Mallavadhani

Keyword(s):

Claisen Rearrangement ◽

Sigmatropic Shift

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Stereochemistry of the SN2' reaction of an acyclic allylic chloride with a secondary amine

Journal of the American Chemical Society ◽

10.1021/ja00467a068 ◽

1977 ◽

Vol 99 (25) ◽

pp. 8368-8370 ◽

Cited By ~ 15

Author(s):

Ronald M. Magid ◽

O. Stanley Fruchey

Keyword(s):

Secondary Amine ◽

Sn2 Reaction ◽

Allylic Chloride

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ChemInform Abstract: Domino Reaction of 3-Nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-Phenylalkylidene)malononitriles: Synthesis of Functionalized 6-(Trifluoromethyl)-6H-dibenzo[b,d]pyrans and a Rare Case of [1,5] Sigmatropic Shift of the Nitro Group

ChemInform ◽

10.1002/chin.201411158 ◽

2014 ◽

Vol 45 (11) ◽

pp. no-no

Author(s):

Vladislav Yu. Korotaev ◽

Alexey Yu. Barkov ◽

Vyacheslav Ya. Sosnovskikh

Keyword(s):

Nitro Group ◽

Rare Case ◽

Domino Reaction ◽

Sigmatropic Shift

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Barrier to 1,3-sigmatropic shift in odd electron ions. A MINDO/3 study of H, OH, CH3 and C6H5 migration

Organic Mass Spectrometry ◽

10.1002/oms.1210171014 ◽

1982 ◽

Vol 17 (10) ◽

pp. 534-536 ◽

Cited By ~ 15

Author(s):

Y. Hoppilliard ◽

G. Bouchoux

Keyword(s):

Sigmatropic Shift

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Preparation of Epoxide Rubber Containing Allylic Chloride

Rubber Chemistry and Technology ◽

10.5254/1.3539275 ◽

1969 ◽

Vol 42 (4) ◽

pp. 1028-1033 ◽

Cited By ~ 1

Author(s):

A. E. Gurgiolo

Keyword(s):

Zinc Oxide ◽

Magnesium Oxide ◽

Propylene Oxide ◽

Indirect Proof ◽

Zinc Oxides ◽

Allylic Chloride

Abstract New epoxide monomers have been prepared that contain allylic chlorine. These have been copolymerized with propylene oxide to give polymers that also contain allylic chlorine. This type of propylene oxide rubber can be vulcanized with a mixture of magnesium oxide and zinc oxide eliminating the need for sulfur in the vulcanization recipe. This work presents an indirect proof of the allylic structure of neoprene and substantiates the theory of vulcanization of neoprene by magnesium and zinc oxides.

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