Effects of (BCO)n Substituent on Claisen Rearrangement of Phenyl Allyl Ether

2007 ◽  
Vol 23 (2) ◽  
pp. 212-216 ◽  
Author(s):  
X PEI ◽  
J JIAN ◽  
H WU
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Ether

scholarly journals Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

2018 ◽  
Vol 14 ◽  
pp. 2991-2998 ◽  
Author(s):  
Christiane Schultze ◽  
Bernd Schmidt
Keyword(s):  
Double Bond ◽  
Olefin Metathesis ◽  
Claisen Rearrangement ◽  
Allylic Oxidation ◽  
Allyl Ether ◽  
Ring Closing Metathesis ◽  
Wittig Olefination

8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.

The carbon analogue of the claisen rearrangement of phenyl allyl ether

Tetrahedron ◽  
1966 ◽  
Vol 22 (2) ◽  
pp. 385-391 ◽  
Author(s):  
W. von E Doering ◽  
R.A. Bragole
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Ether

ChemInform Abstract: THE CLAISEN REARRANGEMENT OF UMBELLIFERONE ALLYL ETHER

1980 ◽  
Vol 11 (16) ◽  
Author(s):  
M. A. LOUTFY
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Ether

Experiments directed towards the synthesis of anthracyclinones. III. β-Formylation of hydroxyanthraquinones by the Claisen rearrangement

1977 ◽  
Vol 30 (8) ◽  
pp. 1743 ◽  
Author(s):  
JL Roberts ◽  
PS Rutledge
Keyword(s):  
Claisen Rearrangement ◽  
Allyl Ether ◽  
Olefinic Bond ◽  
Thermally Induced

β-Formylation of an α-hydroxyanthraquinone is shown to be possible by way of thermally induced rearrangement of the allyl ether, migration of the olefinic bond, and ozonolysis.

Wilzbach tritiation studies. I. Isotope distribution in tritium-labelled anthranilic acid, isopropanol and phenyl allyl ether

1965 ◽  
Vol 18 (3) ◽  
pp. 297 ◽  
Author(s):  
JL Garnett ◽  
SW Law ◽  
AR Till
Keyword(s):  
Anthranilic Acid ◽  
Claisen Rearrangement ◽  
Total Activity ◽  
Hydroxyl Group ◽  
Allyl Ether ◽  
Radical Mechanism ◽  
Isotope Distribution ◽  
Hydrogen Position ◽  
Radiation Induced ◽  
Distribution Studies

Isotope distribution studies with anthranilic acid labelled by the Wilzbach method indicate that positions 3 and 5 have respectively 49.8% and 27.4% of the total activity, tritium incorporation thus tending to be highest at the most electronegative positions. In isopropanol the hydroxyl group contains approximately three times as much isotope as at any other hydrogen position, while tritiation of the secondary C-H is slightly more efficient than the primary C-H. In the tritiation of phenyl ally1 ether, the predominant process is polymerization after reasonable exposure time, little radiation-induced Claisen rearrangement or saturation of the double bond being observed. A free radical mechanism has been proposed to account for the above distributions which have also been compared with results obtained by catalytic exchange. From these model compounds the relative preparative applicability of the Wilzbach and catalytic techniques has been discussed.

A route to large carbocycles using an alicyclic claisen rearrangement.

1982 ◽  
Vol 23 (52) ◽  
pp. 5455-5458
Author(s):  
A Cameron
Keyword(s):  
Claisen Rearrangement

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.

Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

2014 ◽  
Vol 11 (9) ◽  
pp. 677-681 ◽  
Author(s):  
Van-Son Nguyen ◽  
Ling Shi ◽  
Yue Li ◽  
Qiu-An Wang
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Microwave Assistance

Copper-catalyzed alkynylation/annulation cascades of N-allyl ynamides: regioselective access to medium-sized N-heterocycles

2021 ◽  
Vol 8 (1) ◽  
pp. 18-24
Author(s):  
Xu-Heng Yang ◽  
Jian Huang ◽  
Fang Wang ◽  
Zhuoliang Liu ◽  
Yujiao Li ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Synthetic Strategy ◽  
Key Steps

A synthetic strategy based on sequential application of aza-Claisen rearrangement, C–H functionalization, C–N coupling and cyclization as key steps has been developed for the synthesis of 6-, 7-, 8-, and 9-membered rings N-heterocycles.

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